0dwhuldo (6, iru&khp&rpp 7klv - rsc.org file1 9. nmr data 9-a. nmr spectrum of substrates 1h and 13c...

1

9. NMR Data

9-a. NMR spectrum of substrates1H and 13C NMR spectrum of 2a

9 8 7 6 5 4 3 2 1 ppm

-0.000

1.990

4.883

4.905

5.928

5.949

7.182

7.190

7.203

7.215

7.229

7.237

7.246

7.297

7.309

7.319

7.331

3.05

1.01

1.00

4.26

6.04

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

21.09

69.16

76.81

77.23

77.65

127.93

127.98

128.38

128.66

128.81

135.76

136.22

169.62

3

THF

THF

Ph

N3

Ph

OAc

Ph

N3

Ph

OAc

Electronic Supplementary Material (ESI) for ChemComm.This journal is The Royal Society of Chemistry 2016

2

1H and 13C NMR spectrum of 2b

9 8 7 6 5 4 3 2 1 ppm

0.000

2.081

4.971

4.990

5.975

5.994

7.148

7.160

7.165

7.172

7.180

7.260

7.308

7.331

7.337

7.342

7.352

8.122

8.145

8.151

3.00

1.00

1.00

2.03

5.11

1.98

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

20.92

68.52

76.81

76.92

77.23

77.65

123.32

127.66

128.82

128.87

129.12

134.81

143.01

148.02

169.45

THF

Ph

N3OAc

NO2

Ph

N3OAc

NO2

3

1H and 13C NMR spectrum of 2c

9 8 7 6 5 4 3 2 1 ppm

0.000

2.145

3.743

4.727

4.756

5.872

5.900

6.730

6.737

6.753

6.759

6.769

6.960

6.970

6.976

6.992

6.999

7.076

7.089

7.094

7.100

7.108

7.122

7.194

7.205

7.215

7.250

2.98

3.06

1.00

1.00

2.00

1.99

2.04

3.02

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

21.32

55.40

69.42

76.81

77.23

77.66

78.70

113.49

114.07

127.54

128.45

128.58

129.24

136.86

159.83

169.94

THF

N3OAc

PhMeO

N3OAc

PhMeO

4

1H and 13C NMR spectrum of 2d

9 8 7 6 5 4 3 2 1 ppm

0.000

1.172

1.193

2.039

4.737

4.753

5.104

5.120

5.125

5.141

5.147

5.162

5.168

5.184

7.258

7.293

7.299

7.305

7.321

7.328

7.331

7.345

7.346

7.358

7.359

7.372

7.377

7.380

7.383

7.387

7.398

7.404

7.411

3.12

3.07

1.00

1.02

5.25

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

14.81

21.27

68.53

73.20

76.80

77.23

77.65

127.48

128.59

128.85

136.12

170.38

THF

Ph

N3OAc

Ph

N3OAc

5

1H and 13C NMR spectrum of 2e

9 8 7 6 5 4 3 2 1 ppm

-0.001

1.261

1.487

1.490

1.504

1.514

1.527

1.534

1.539

1.557

1.565

1.589

1.935

1.958

1.981

1.984

2.005

2.027

2.031

2.054

2.086

4.524

4.548

4.904

4.909

4.913

4.939

4.943

4.960

4.965

4.971

4.976

5.154

5.172

5.179

5.196

5.203

5.221

5.259

5.609

5.630

5.643

5.652

5.665

5.687

5.699

5.709

5.721

5.743

7.252

7.277

7.282

7.294

7.301

7.308

7.334

7.347

7.355

7.370

7.375

7.380

7.394

7.400

7.409

1.99

2.07

3.00

0.99

2.02

1.05

1.00

5.11

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

21.04

29.39

30.43

68.44

74.86

76.80

77.23

77.65

115.44

127.75

128.93

129.00

136.10

137.23

170.36

THF

Ph

N3OAc

Ph

N3OAc

6

1H and 13C NMR spectrum of 2f

9 8 7 6 5 4 3 2 1 ppm

0.000

1.067

1.090

1.199

1.222

2.132

3.751

3.773

3.797

3.821

3.843

5.627

5.652

5.760

5.776

7.258

7.302

7.320

7.324

7.331

7.337

7.344

7.351

7.359

7.368

7.375

7.382

7.394

3.04

0.11

3.10

1.05

1.00

0.03

5.18

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

16.39

21.25

60.93

76.80

77.23

77.65

79.11

127.35

128.85

128.91

137.36

170.02

THF

N3OAc

Ph

N3OAc

Ph

diastereomer diastereomer

7

1H and 13C NMR spectrum of 2g

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

16.30

21.19

60.80

76.81

77.23

77.65

78.37

115.72

116.00

129.11

129.22

129.32

133.24

133.28

161.35

164.63

169.92

THF

N3OAc

F

N3OAc

F

diastereomerdiastereomer

8

1H and 13C NMR spectrum of 2i

9 8 7 6 5 4 3 2 1 ppm

1.279

1.284

1.295

1.303

1.310

1.317

1.326

1.332

1.340

1.349

1.359

1.365

1.369

1.378

1.393

1.399

1.451

1.476

1.500

1.508

1.515

1.521

1.527

1.533

1.545

1.558

1.565

2.129

2.139

3.574

3.588

3.599

3.604

3.612

3.617

3.628

3.642

3.659

3.675

3.691

5.694

5.719

5.797

5.813

7.257

7.321

7.324

7.331

7.336

7.345

7.352

7.361

7.368

7.376

7.382

7.395

3.38

3.39

1.36

2.96

0.30

1.09

1.00

0.09

5.60

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

13.83

19.47

21.24

32.75

65.96

76.81

77.23

77.66

78.46

127.34

128.88

137.62

169.99

THF

OAcN3

Ph

OAcN3

Ph

diastereomer

diastereomer

9

1H and 13C NMR spectrum of 2j

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

1.213

1.222

1.237

1.246

1.255

1.269

1.281

1.292

1.304

1.315

1.338

1.354

1.377

1.401

1.412

1.422

1.433

1.444

1.454

1.466

1.491

1.498

1.515

1.522

1.532

1.551

1.560

1.579

1.592

1.610

1.624

1.637

1.655

2.005

3.378

3.390

3.400

3.412

3.421

3.434

4.864

4.875

4.887

4.897

4.908

4.919

7.294

6.23

8.52

3.10

1.00

1.00

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

13.61

13.70

18.65

19.65

20.73

31.05

32.20

64.69

75.44

76.80

77.23

77.66

170.29

THF

N3

OAc

N3

OAc

10

1H and 13C NMR spectrum of 2q

9 8 7 6 5 4 3 2 1 ppm

2.164

3.440

3.453

3.484

3.497

3.635

3.663

3.679

3.706

5.941

5.954

5.968

5.981

7.351

7.375

7.403

7.412

7.431

7.438

7.456

7.462

7.554

7.579

7.606

3.09

1.04

1.04

1.00

5.16

4.22

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

21.14

55.08

74.50

76.80

77.23

77.65

127.01

127.19

127.56

127.66

128.92

136.17

140.49

141.74

169.97

THF

OAcN3

Ph

OAcN3

Ph

11

1H and 13C NMR spectrum of 2v

9 8 7 6 5 4 3 2 1 ppm

0.000

1.930

1.934

1.952

1.957

1.975

1.980

1.998

2.002

2.025

2.088

2.149

2.159

2.170

2.180

2.192

2.202

2.215

2.226

2.236

2.247

2.889

2.911

2.933

4.584

4.606

5.122

5.132

5.143

5.150

5.153

5.160

5.171

5.181

7.135

7.149

7.154

7.165

7.244

7.255

7.261

7.274

7.362

7.373

7.377

7.392

1.17

3.17

1.21

2.21

1.07

1.08

1.10

2.30

1.10

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

21.37

25.39

26.04

62.48

72.77

76.81

77.23

77.65

126.75

128.54

129.06

129.25

131.87

136.21

170.52

THF

N3OAc

N3OAc

12

1H and 13C NMR spectrum of 2w

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

1.492

1.508

1.547

1.574

1.598

1.621

1.625

1.628

1.634

1.648

1.665

1.671

1.686

1.696

1.701

1.716

1.728

1.735

1.763

1.781

1.792

1.804

1.809

1.815

1.827

1.832

1.839

1.853

1.858

1.864

1.870

1.886

1.900

1.912

2.049

2.087

2.120

3.545

3.557

3.573

3.585

3.602

3.614

4.792

4.804

4.820

4.831

4.848

4.859

7.271

4.33

3.85

2.15

3.05

1.01

1.00

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

21.48

22.58

23.56

27.92

30.18

31.09

66.49

76.81

77.23

77.65

78.65

170.42

THF

N3 OAc

N3 OAc

13

1H and 13C NMR spectrum of 4a

9 8 7 6 5 4 3 2 1 ppm

0.000

0.991

1.016

1.042

2.227

2.252

2.277

2.303

4.877

4.899

5.944

5.966

7.188

7.196

7.209

7.221

7.233

7.242

7.295

7.304

7.311

7.321

7.325

3.10

2.06

1.00

1.00

4.15

6.22

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

9.09

27.79

69.26

76.81

77.23

77.40

77.65

127.87

128.00

128.38

128.63

128.78

135.82

136.39

172.98

THF

PhO

N3

Ph O

PhO

N3

Ph O

14


9 8 7 6 5 4 3 2 1 ppm

0.000

0.981

1.004

1.026

1.050

2.402

2.426

2.449

2.472

2.495

2.519

2.542

4.853

4.876

5.927

5.950

7.205

7.212

7.224

7.233

7.238

7.244

7.257

7.288

7.300

7.307

7.314

7.322

7.330

3.01

3.04

0.98

1.00

1.00

4.26

6.14

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

18.80

18.83

34.19

69.41

76.80

77.14

77.23

77.65

127.76

128.04

128.40

128.64

128.74

128.79

135.89

136.62

175.47

THF

PhO

N3

Ph O

PhO

N3

Ph O

15


9 8 7 6 5 4 3 2 1 ppm

0.000

1.060

4.832

4.856

5.896

5.920

7.207

7.215

7.225

7.239

7.249

7.280

7.291

7.300

7.306

7.314

7.322

9.05

1.00

1.00

4.24

6.05

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

27.03

38.89

69.59

76.81

77.23

77.66

127.59

128.03

128.39

128.62

128.68

128.78

135.95

136.81

176.83

THF

PhO

N3

Ph O

PhO

N3

Ph O

16


9 8 7 6 5 4 3 2 1 ppm

0.000

1.834

1.839

1.857

1.863

4.942

4.962

5.797

5.802

5.808

5.813

5.848

5.854

5.860

5.865

5.998

6.018

6.904

6.928

6.951

6.956

6.974

6.979

7.002

7.025

7.159

7.167

7.179

7.184

7.190

7.196

7.205

7.233

7.260

7.269

7.276

7.282

7.287

7.291

7.295

7.302

7.309

3.02

1.00

1.01

1.00

1.07

4.33

6.42

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

18.24

69.17

76.81

77.23

77.51

77.65

122.26

127.83

127.92

128.23

128.55

128.64

128.67

135.65

136.17

146.09

164.98

THF

PhO

N3

Ph O

PhO

N3

Ph O

17


9 8 7 6 5 4 3 2 1 ppm

0.000

3.920

3.925

4.893

4.915

5.958

5.980

7.191

7.199

7.213

7.224

7.239

7.247

7.262

7.289

7.301

7.310

7.317

7.322

1.94

1.00

1.00

4.16

5.99

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

40.76

68.86

76.81

77.23

77.65

79.08

127.80

127.97

128.46

128.70

128.97

129.10

135.20

135.37

165.89

THF

PhO

N3

Ph OCl

PhO

N3

Ph OCl

18


9 8 7 6 5 4 3 2 1 ppm

2.496

2.505

2.514

2.527

2.547

2.571

2.575

2.591

2.604

2.613

2.622

3.624

4.897

4.918

5.937

5.958

7.171

7.182

7.194

7.199

7.206

7.215

7.284

7.293

7.295

7.308

7.314

7.330

4.10

2.93

0.99

1.00

3.94

5.92

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.95

29.38

52.01

69.13

76.81

77.23

77.66

77.99

127.88

127.96

128.36

128.67

128.82

128.83

135.67

135.98

170.87

172.51

THF

PhO

N3

Ph OOMe

O

PhO

N3

Ph OOMe

O

19


9 8 7 6 5 4 3 2 1 ppm

0.000

5.069

5.089

6.183

6.202

7.216

7.219

7.222

7.233

7.238

7.248

7.257

7.268

7.282

7.290

7.298

7.308

7.312

7.315

7.325

7.330

7.338

7.346

7.353

7.387

7.390

7.395

7.414

7.418

7.435

7.440

7.510

7.515

7.519

7.532

7.539

7.546

7.559

7.564

7.568

7.995

8.000

8.023

1.02

1.00

10.43

2.31

1.20

2.08

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

69.41

76.80

77.23

77.65

78.36

127.82

127.98

128.36

128.64

128.65

128.81

129.87

129.90

133.45

135.60

136.13

165.26

THF

PhO

N3

Ph

Ph

O

PhO

N3

Ph

Ph

O

20

1H and 13C NMR spectrum of 4h

9 8 7 6 5 4 3 2 1 ppm

0.001

5.034

5.053

6.151

6.171

6.454

6.460

6.466

6.471

7.182

7.194

7.196

7.207

7.219

7.232

7.244

7.251

7.269

7.282

7.290

7.299

7.317

7.543

7.546

7.549

1.00

1.00

1.00

11.13

1.07

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

69.13

76.81

77.23

77.65

78.07

112.07

118.77

127.80

127.98

128.31

128.58

128.78

128.83

135.31

135.69

144.20

146.97

157.19

THF

PhO

N3

Ph O

O

PhO

N3

Ph O

O

21


9 8 7 6 5 4 3 2 1 ppm

0.000

5.025

5.044

6.117

6.137

7.064

7.077

7.081

7.093

7.223

7.239

7.247

7.256

7.290

7.298

7.304

7.543

7.547

7.560

7.564

7.784

7.788

7.796

7.800

1.00

1.00

1.10

10.29

1.09

1.02

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

71.07

78.59

79.01

79.44

80.20

129.50

129.81

130.13

130.38

130.57

130.59

134.92

134.94

135.95

137.17

137.72

162.53

THF

PhO

N3

Ph O

S

PhO

N3

Ph O

S

22


9 8 7 6 5 4 3 2 1 ppm

0.000

1.337

4.882

4.905

5.702

5.725

7.242

7.246

7.256

7.263

7.272

7.280

7.289

7.305

7.316

7.324

7.334

7.337

7.341

8.92

1.00

1.00

10.13

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

27.79

69.23

76.81

77.23

77.65

80.12

82.87

127.94

128.16

128.40

128.67

128.79

128.88

135.77

136.16

152.44

THF

PhO

N3

Ph

O

O

PhO

N3

Ph

O

O

23

9-b. NMR spectrum of -amido ketones1H and 13C NMR spectrum of 3a

9 8 7 6 5 4 3 2 1 ppm

0.000

2.034

6.574

6.599

7.009

7.032

7.217

7.242

7.251

7.263

7.270

7.276

7.296

7.301

7.317

7.323

7.330

7.366

7.374

7.378

7.384

7.390

7.400

7.406

7.411

7.416

7.481

7.486

7.490

7.504

7.510

7.517

7.531

7.535

7.539

7.953

7.958

7.964

7.982

3.08

1.00

1.01

3.33

4.14

1.15

2.04

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

23.45

58.63

76.81

77.23

77.65

128.39

128.56

128.90

129.31

129.39

133.99

134.47

137.48

169.38

196.07

THF

Ph

NHAcO

Ph

Ph

NHAcO

Ph

24


9 8 7 6 5 4 3 2 1 ppm

0.000

2.046

6.560

6.584

6.995

7.018

7.283

7.301

7.328

7.352

7.378

8.092

8.121

8.210

8.239

3.17

1.00

1.04

5.18

2.03

2.04

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

23.16

59.41

76.80

77.23

77.65

123.99

128.42

129.08

129.68

130.14

135.89

139.21

150.50

169.61

194.84

THF

Ph

NHAcO

NO2

Ph

NHAcO

NO2

25


9 8 7 6 5 4 3 2 1 ppm

0.000

2.017

3.720

6.529

6.554

6.797

6.826

7.291

7.319

7.353

7.377

7.403

7.469

7.493

7.944

7.948

7.972

3.07

3.04

1.00

2.04

1.02

4.17

1.06

2.03

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

23.35

55.33

58.01

76.81

77.23

77.65

114.72

128.81

129.22

129.50

129.62

133.80

134.53

159.64

169.38

196.13

THF

NHAcO

PhMeO

NHAcO

PhMeO

26


9 8 7 6 5 4 3 2 1 ppm

0.000

1.989

2.105

5.555

5.577

6.935

7.303

7.306

7.325

7.339

7.346

7.359

7.369

3.01

3.06

1.00

0.99

5.20

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

23.16

27.31

63.63

76.80

77.23

77.65

128.12

128.74

129.36

136.56

169.47

203.81

THF

Ph

NHAcO

Ph

NHAcO

27


9 8 7 6 5 4 3 2 1 ppm

0.000

1.258

1.981

2.193

2.198

2.220

2.225

2.243

2.247

2.265

2.269

2.289

2.312

2.430

2.464

2.487

2.512

2.536

4.887

4.921

4.925

4.936

4.941

4.946

5.565

5.587

5.611

5.622

5.626

5.632

5.643

5.648

5.665

5.669

5.680

5.691

5.702

5.723

6.966

6.985

7.283

7.289

7.294

7.298

7.316

7.330

7.338

7.359

7.382

7.391

3.11

2.12

2.05

2.00

1.06

0.95

0.98

5.24

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

23.14

27.57

38.96

63.08

76.81

77.23

77.65

115.66

128.18

128.71

129.31

136.46

136.51

169.47

205.43

THF

Ph

NHAcO

Ph

NHAcO

28


9 8 7 6 5 4 3 2 1 ppm

1.418

1.441

2.062

5.535

5.559

5.583

5.607

5.630

6.749

7.290

7.318

7.408

7.428

7.476

7.501

7.527

7.594

7.619

7.643

7.987

8.011

3.07

3.00

1.00

0.95

2.05

1.07

2.00

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

19.96

23.48

50.20

76.81

77.23

77.65

128.89

129.05

134.00

134.11

169.64

199.33

THF

NHAcO

Ph

NHAcO

Ph

29


9 8 7 6 5 4 3 2 1 ppm

-0.000

1.409

1.412

1.433

1.435

2.057

2.060

5.502

5.526

5.550

5.574

5.597

6.706

7.148

7.151

7.178

7.198

7.205

7.297

8.020

8.039

8.048

8.066

2.97

3.19

1.00

0.95

1.98

1.97

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

19.80

23.41

50.01

76.81

77.23

77.66

116.13

116.42

131.57

131.69

164.65

168.05

169.66

197.83

THF

NHAcO

F

NHAcO

F

30


9 8 7 6 5 4 3 2 1 ppm

-0.000

1.411

1.434

2.055

3.887

5.478

5.501

5.525

5.548

5.572

6.759

6.954

6.983

7.290

7.969

7.998

3.02

3.18

2.98

1.00

1.00

2.09

1.99

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

20.30

23.53

49.83

55.71

76.81

77.23

77.65

114.25

126.78

131.28

164.33

169.58

197.68

THF

NHAcO

OMe

NHAcO

OMe

31


9 8 7 6 5 4 3 2 1 ppm

1.309

1.325

1.341

1.356

1.366

1.376

1.390

1.400

1.425

1.444

1.522

1.539

1.546

1.556

1.568

1.584

1.592

1.597

1.602

1.609

1.619

1.627

1.644

1.850

1.868

1.885

1.901

1.914

1.919

1.931

1.950

2.068

5.613

5.628

5.638

5.654

5.664

5.679

6.553

6.577

7.280

7.473

7.497

7.523

7.588

7.592

7.606

7.613

7.637

7.981

7.986

8.009

3.06

2.50

1.07

1.03

3.09

1.00

0.97

2.00

1.02

2.01

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

14.01

18.48

23.50

35.72

53.82

76.81

77.23

77.65

128.82

129.05

134.02

134.74

169.93

199.46

THF

NHAcO

Ph

NHAcO

Ph

32


7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

1.337

1.352

1.361

1.381

1.386

1.405

1.474

1.491

1.498

1.508

1.515

1.520

1.532

1.537

1.544

1.549

1.554

1.561

1.569

1.578

1.593

1.617

1.642

1.666

1.691

1.798

1.813

1.816

1.832

1.844

1.849

1.852

1.859

1.862

1.867

1.879

1.895

1.914

2.023

2.465

2.487

2.491

2.511

2.516

4.625

4.640

4.650

4.665

4.674

4.690

6.358

6.378

7.300

6.19

2.20

1.15

2.00

1.09

3.08

2.04

1.00

0.99

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

13.84

14.04

17.13

18.47

23.34

33.77

42.00

58.01

76.81

77.23

77.66

170.01

209.59

THF

NHAc

O

NHAc

O

33

1H and 13C NMR spectrum of 3k

9 8 7 6 5 4 3 2 1 ppm

0.000

2.114

4.771

4.785

6.682

7.477

7.482

7.501

7.527

7.601

7.605

7.609

7.623

7.629

7.636

7.650

7.654

7.658

7.968

7.973

7.997

3.09

2.00

1.02

2.09

1.19

2.06

200 180 160 140 120 100 80 60 40 20 0 ppm

23.24

46.71

76.81

77.23

77.65

128.09

129.10

134.35

134.49

170.49

194.42

THF

ONHAc

ONHAc

34

1H and 13C NMR spectrum of 3l

9 8 7 6 5 4 3 2 1 ppm

0.000

2.108

2.426

4.736

4.750

6.712

7.279

7.289

7.306

7.864

7.892

3.06

3.05

2.00

1.02

2.14

2.09

200 180 160 140 120 100 80 60 40 20 0 ppm

21.90

23.21

46.55

76.80

77.23

77.65

128.15

129.74

132.00

145.35

170.43

193.95

THF

ONHAc

H3C

ONHAc

H3C

35

1H and 13C NMR spectrum of 3m

9 8 7 6 5 4 3 2 1 ppm

0.000

2.106

3.884

4.707

4.721

6.718

6.937

6.947

6.953

6.970

6.976

6.986

7.293

7.934

7.944

7.950

7.967

7.973

7.983

3.17

3.08

2.00

0.98

2.06

2.05

200 180 160 140 120 100 80 60 40 20 0 ppm

23.22

46.28

55.71

76.81

77.23

77.65

114.24

127.48

130.39

164.42

170.42

192.74

THF

ONHAc

MeO

ONHAc

MeO

36

1H and 13C NMR spectrum of 3n

9 8 7 6 5 4 3 2 1 ppm

0.000

2.115

4.742

4.757

6.663

7.143

7.152

7.159

7.181

7.202

7.209

7.219

7.291

7.990

8.000

8.007

8.017

8.023

8.029

8.040

8.047

8.056

3.03

2.00

1.02

2.07

2.05

200 180 160 140 120 100 80 60 40 20 0 ppm

23.20

46.56

76.80

77.23

77.65

116.20

116.49

130.76

130.89

130.94

130.98

164.75

168.16

170.48

192.89

THF

ONHAc

F

ONHAc

F

37

1H and 13C NMR spectrum of 3o

9 8 7 6 5 4 3 2 1 ppm

0.000

2.113

4.736

4.751

6.645

7.289

7.466

7.494

7.910

7.939

3.05

2.00

0.99

2.04

2.07

200 180 160 140 120 100 80 60 40 20 0 ppm

23.20

46.65

76.81

77.23

77.43

77.65

129.47

132.81

140.88

170.48

193.33

THF

ONHAc

Cl

ONHAc

Cl

38

1H and 13C NMR spectrum of 3p

9 8 7 6 5 4 3 2 1 ppm

0.000

2.121

4.781

4.796

6.533

7.278

7.810

7.837

8.072

8.099

3.06

2.00

0.98

2.03

2.04

200 180 160 140 120 100 80 60 40 20 0 ppm

23.16

46.95

76.81

77.23

77.66

117.51

117.76

128.53

132.95

137.43

170.53

193.45

THF

ONHAc

NC

ONHAc

NC

39

1H and 13C NMR spectrum of 3q

9 8 7 6 5 4 3 2 1 ppm

0.000

2.119

4.790

4.804

6.662

7.265

7.385

7.409

7.418

7.428

7.433

7.437

7.451

7.476

7.493

7.499

7.504

7.613

7.636

7.641

7.698

7.726

8.034

8.062

3.06

2.00

0.99

3.15

2.06

2.05

2.06

200 180 160 140 120 100 80 60 40 20 0 ppm

23.22

46.71

76.81

77.23

77.65

127.40

127.63

128.66

129.16

133.12

139.59

146.95

170.47

193.94

THF

ONHAc

Ph

ONHAc

Ph

40

1H and 13C NMR spectrum of 3r

9 8 7 6 5 4 3 2 1 ppm

0.000

2.138

4.896

4.911

6.752

7.539

7.542

7.565

7.588

7.592

7.598

7.603

7.625

7.629

7.648

7.652

7.859

7.888

7.917

7.934

7.961

7.990

7.995

8.019

8.024

8.501

3.08

2.00

1.00

2.06

4.18

1.02

200 180 160 140 120 100 80 60 40 20 0 ppm

23.26

46.77

76.80

77.23

77.65

123.31

127.28

127.99

129.00

129.21

129.82

130.13

131.72

132.53

136.15

170.51

194.26

THF

ONHAc

ONHAc

41

1H and 13C NMR spectrum of 3s

9 8 7 6 5 4 3 2 1 ppm

0.000

0.072

2.003

3.739

4.174

4.189

6.237

7.199

7.220

7.225

7.257

7.266

7.282

7.291

7.299

7.304

7.316

7.335

7.340

7.356

7.362

7.369

3.03

1.98

2.00

0.94

5.49

220 200 180 160 140 120 100 80 60 40 20 0 ppm

23.10

47.89

48.97

76.81

77.23

77.65

127.71

129.17

129.51

133.02

170.31

203.28

THF

ONHAc

ONHAc

42

1H and 13C NMR spectrum of 3u

8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

1.649

1.664

1.678

1.691

1.707

1.721

1.733

1.743

1.753

1.788

1.799

1.819

1.830

1.842

1.869

1.878

1.913

1.950

2.021

2.113

2.122

2.132

2.142

2.153

2.165

2.176

2.185

2.349

2.369

2.394

2.414

2.438

2.458

2.505

2.512

2.549

2.556

2.631

2.641

2.651

2.661

2.672

2.683

2.693

2.703

4.441

4.462

4.482

4.503

4.523

6.482

1.28

1.31

2.20

3.04

1.13

1.12

1.02

1.08

1.00

1.05

200 180 160 140 120 100 80 60 40 20 0 ppm

25.13

25.88

29.93

37.42

43.02

60.01

78.50

78.92

79.34

171.56

209.76

THF

ONHAc

ONHAc

43

1H and 13C NMR spectrum of 3v

9 8 7 6 5 4 3 2 1 ppm

0.000

2.242

2.407

2.420

2.428

2.445

2.454

2.469

2.491

2.507

2.529

2.555

2.776

2.784

2.797

2.805

2.838

2.847

2.859

2.868

2.990

2.998

3.012

3.020

3.042

3.050

3.063

3.072

3.232

3.253

3.270

3.284

3.290

3.304

3.321

3.342

5.650

5.673

6.491

6.509

7.134

7.141

7.149

7.160

7.170

7.174

7.206

7.220

7.238

7.249

7.253

7.263

7.267

7.275

7.281

7.297

7.306

3.05

1.21

1.11

1.12

1.09

1.00

0.99

1.03

3.63

200 180 160 140 120 100 80 60 40 20 0 ppm

23.41

27.26

35.52

59.69

76.80

77.23

77.65

124.38

127.51

127.57

127.90

133.57

136.44

170.95

206.64

THF

NHAcO

NHAcO

44

1H and 13C NMR spectrum of 3w

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

1.439

1.453

1.472

1.486

1.500

1.519

1.533

1.670

1.681

1.691

1.702

1.717

1.728

1.739

1.751

1.764

1.781

1.796

1.812

1.823

1.843

1.864

1.895

1.906

1.946

2.017

2.051

2.062

2.076

2.088

2.107

2.121

2.129

2.136

2.409

2.422

2.445

2.467

2.481

2.503

2.518

2.637

2.653

2.683

2.695

2.711

4.658

4.669

4.680

4.691

4.702

4.713

4.723

6.705

1.18

1.17

5.22

2.95

1.15

1.05

1.03

1.00

0.98

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

23.20

23.35

27.64

29.06

32.87

41.63

58.97

76.80

77.23

77.65

169.39

210.46

THF

AcHN O

AcHN O

45

1H and 13C NMR spectrum of 5a

9 8 7 6 5 4 3 2 1 ppm

0.000

1.111

1.137

1.162

2.228

2.236

2.253

2.261

2.278

2.286

2.303

2.312

6.589

6.613

7.039

7.061

7.138

7.203

7.227

7.237

7.250

7.264

7.290

7.312

7.353

7.379

7.404

7.470

7.494

7.519

7.960

7.985

3.07

2.07

1.00

1.02

3.35

4.00

1.11

2.04

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

9.67

29.59

58.46

76.80

77.23

77.65

128.35

128.44

128.82

129.23

129.31

133.90

134.48

137.50

173.03

196.16

THF

Ph

HNO

Ph

O

Ph

HNO

Ph

O

46


9 8 7 6 5 4 3 2 1 ppm

0.000

1.121

1.144

1.168

1.190

2.384

2.407

2.430

2.453

2.476

2.499

6.546

6.570

6.957

6.979

7.212

7.224

7.236

7.245

7.254

7.261

7.273

7.278

7.292

7.298

7.313

7.320

7.326

7.369

7.374

7.394

7.415

7.420

7.482

7.487

7.491

7.505

7.512

7.519

7.532

7.536

7.540

7.957

7.961

7.968

7.985

7.989

7.995

3.01

3.05

0.99

1.00

0.98

3.44

3.96

1.05

1.99

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

19.56

29.84

35.54

58.42

76.81

77.23

77.65

128.32

128.42

128.83

129.24

129.31

133.88

134.59

137.52

176.26

196.27

THF

Ph

HNO

Ph

O

Ph

HNO

Ph

O

47


9 8 7 6 5 4 3 2 1 ppm

-0.000

1.216

6.509

6.533

7.187

7.201

7.205

7.213

7.224

7.233

7.248

7.265

7.290

7.313

7.358

7.382

7.401

7.407

7.445

7.472

7.496

7.521

7.959

7.963

7.987

9.04

1.00

4.23

4.05

1.06

2.00

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

27.58

38.86

58.61

76.80

77.23

77.65

128.31

128.39

128.84

129.23

129.30

133.90

134.53

137.50

177.83

196.30

THF

Ph

HNO

Ph

O

Ph

HNO

Ph

O

48


210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

17.87

58.49

76.80

77.23

77.65

124.83

128.38

128.41

128.82

129.25

129.28

133.89

134.47

137.46

140.82

165.07

196.07

THF

Ph

HNO

Ph

O

Ph

HNO

Ph

O

49


9 8 7 6 5 4 3 2 1 ppm

0.000

4.000

4.051

4.063

4.114

6.513

6.537

7.259

7.265

7.274

7.283

7.287

7.297

7.322

7.337

7.344

7.350

7.377

7.402

7.426

7.498

7.523

7.548

7.957

7.961

7.985

8.083

8.104

2.07

1.00

3.72

4.03

1.17

2.06

0.97

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

42.71

58.94

76.80

77.23

77.65

128.44

128.86

128.96

129.32

129.50

134.16

136.65

165.43

194.95

THF

Ph

HN

Ph

O

OCl

Ph

HN

Ph

O

OCl

50


9 8 7 6 5 4 3 2 1 ppm

0.000

2.527

2.547

2.557

2.574

2.588

2.598

2.607

2.617

2.630

2.639

2.647

2.651

2.675

3.631

6.558

6.582

7.199

7.204

7.212

7.223

7.233

7.241

7.246

7.252

7.260

7.271

7.279

7.284

7.300

7.307

7.313

7.351

7.356

7.374

7.388

7.395

7.401

7.465

7.469

7.473

7.487

7.494

7.501

7.514

7.518

7.946

7.951

7.975

4.08

3.07

1.00

4.28

4.04

1.21

2.00

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

29.25

30.86

51.89

58.67

76.80

77.23

77.65

128.32

128.45

128.80

129.20

129.27

133.87

134.41

137.24

170.67

173.28

195.80

THF

Ph

HN

Ph

O

OOMe

O

Ph

HN

Ph

O

OOMe

O

51


9 8 7 6 5 4 3 2 1 ppm

0.000

6.753

6.776

7.210

7.214

7.224

7.234

7.243

7.248

7.253

7.258

7.262

7.280

7.300

7.305

7.322

7.328

7.333

7.373

7.379

7.385

7.397

7.401

7.407

7.413

7.423

7.432

7.454

7.458

7.471

7.482

7.484

7.494

7.499

7.509

7.530

7.534

7.772

7.795

7.828

7.833

7.856

1.00

3.18

4.07

4.04

0.97

2.08

2.04

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

59.06

76.81

77.23

77.65

127.33

128.50

128.58

128.70

128.91

129.34

129.39

131.88

134.03

134.41

137.40

166.50

196.00

THF

Ph

NHO

Ph

O

Ph

Ph

NHO

Ph

O

Ph

52


210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

58.26

76.81

77.23

77.66

112.20

114.81

128.44

128.58

128.84

129.26

129.36

133.96

134.31

137.17

144.32

147.69

157.49

195.44

THF

Ph

NHO

Ph

OO

Ph

NHO

Ph

OO

53


9 8 7 6 5 4 3 2 1 ppm

0.000

6.721

6.744

7.004

7.017

7.032

7.192

7.216

7.239

7.256

7.281

7.304

7.351

7.376

7.401

7.421

7.445

7.470

7.488

7.513

7.582

7.592

7.686

7.709

7.984

8.009

1.00

1.05

3.22

5.93

1.02

1.04

2.02

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

58.93

76.80

77.23

77.65

127.76

128.48

128.55

128.63

128.85

129.28

129.32

130.53

134.00

134.25

137.16

138.58

161.06

195.74

THF

Ph

NHO

Ph

OS

Ph

NHO

Ph

OS

54


9 8 7 6 5 4 3 2 1 ppm

0.000

1.427

6.026

6.049

6.268

6.293

7.206

7.218

7.229

7.239

7.252

7.258

7.267

7.292

7.308

7.315

7.320

7.354

7.377

7.403

7.465

7.490

7.514

7.943

7.968

9.15

1.04

1.00

3.50

4.34

1.21

2.23

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

28.53

59.93

76.80

77.23

77.65

80.07

128.27

128.44

128.82

129.20

129.32

133.77

134.71

137.69

155.17

196.28

THF

Ph

HNO

Ph

Boc

Ph

HNO

Ph

Boc

55

9-c. NMR spectrum of oxazoles and a thiazole1H and 13C NMR spectrum of 6a

9 8 7 6 5 4 3 2 1 ppm

-0.000

2.534

7.283

7.286

7.300

7.308

7.319

7.327

7.333

7.344

7.352

7.362

7.373

7.558

7.562

7.577

7.583

7.589

7.622

7.626

7.648

7.654

3.00

6.02

2.04

2.00

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

14.12

76.81

77.23

77.65

126.54

127.96

128.13

128.48

128.68

128.76

129.21

132.67

135.27

145.42

160.31

THF

N

O

Ph

Ph

N

O

Ph

Ph

56


12 11 10 9 8 7 6 5 4 3 2 1 ppm

0.000

2.927

2.951

2.975

3.172

3.197

3.221

7.255

7.306

7.312

7.316

7.326

7.328

7.336

7.343

7.350

7.356

7.362

7.368

7.375

7.381

7.391

7.545

7.550

7.555

7.564

7.570

7.577

7.601

7.606

7.620

7.627

7.633

9.811

2.02

2.00

5.98

1.99

1.96

0.85

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

23.42

31.13

76.81

77.23

77.65

126.65

128.18

128.39

128.77

128.85

128.92

132.22

135.08

145.75

162.10

176.97

THF

N

O

Ph

PhOH

O

N

O

Ph

PhOH

O

57

1H and 13C NMR spectrum of 5k

9 8 7 6 5 4 3 2 1 ppm

0.000

1.534

1.549

1.558

1.573

3.695

3.719

3.743

3.755

3.767

3.779

3.803

3.826

3.881

6.495

6.518

6.531

6.555

6.978

7.001

7.061

7.090

7.101

7.108

7.117

7.125

7.130

7.139

7.146

7.154

7.164

7.173

7.187

7.196

7.200

7.213

7.219

7.223

7.230

7.235

7.249

7.255

7.265

7.276

7.288

7.293

7.316

7.342

7.347

7.373

7.387

7.393

7.415

7.421

7.439

7.445

7.459

7.465

7.520

7.583

7.612

7.640

2.94

2.97

2.15

6.07

0.97

1.00

1.07

1.08

28.32

4.05

200 180 160 140 120 100 80 60 40 20 0 ppm

18.79

46.81

47.08

55.43

58.80

76.80

77.23

77.65

105.74

105.80

119.10

119.17

126.14

126.37

126.39

126.41

127.52

127.64

128.23

128.37

128.43

128.77

128.82

129.10

129.16

129.18

129.28

129.44

129.47

133.78

133.84

133.88

133.92

134.34

134.49

136.30

136.47

137.01

137.35

157.76

157.80

173.52

173.67

195.64

195.85

THF

Ph

NH

O

O

Ph

MeO

Ph

NH

O

O

Ph

MeO

58


9 8 7 6 5 4 3 2 1 ppm

-0.000

1.850

1.874

3.886

4.450

4.474

4.498

4.523

7.105

7.113

7.121

7.143

7.151

7.228

7.257

7.275

7.300

7.314

7.328

7.337

7.363

7.385

7.391

7.494

7.499

7.512

7.518

7.520

7.537

7.543

7.655

7.677

7.682

7.698

7.727

7.748

2.96

3.16

1.00

2.22

6.42

3.09

5.27

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

20.29

39.86

55.45

76.80

77.23

77.65

105.76

119.14

125.94

126.42

126.63

127.43

128.18

128.23

128.49

128.72

129.14

129.24

129.48

132.84

133.80

135.30

137.19

145.53

157.78

165.45

THF

N

O

Ph

Ph

OMe

N

O

Ph

Ph

OMe

59

1H and 13C NMR spectrum of 7

9 8 7 6 5 4 3 2 1 ppm

-0.000

2.728

7.240

7.245

7.255

7.263

7.278

7.292

7.313

7.479

7.484

7.496

7.499

7.509

3.00

8.63

2.11

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

19.37

76.81

77.23

77.65

127.78

128.05

128.41

128.80

129.14

129.70

132.33

132.54

135.08

149.58

163.92

THF

N

S

Ph

Ph

N

S

Ph

Ph

60

9-d. NMR spectrum of 8 and 91H and 13C NMR spectrum of 8

9 8 7 6 5 4 3 2 1 ppm

0.000

4.895

4.909

5.374

5.396

5.410

5.417

5.431

5.453

7.292

7.305

7.314

7.321

7.335

7.361

7.383

7.408

7.434

7.503

7.527

7.552

8.019

8.023

8.047

3.05

0.99

1.00

6.99

1.06

2.00

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

14.78

68.82

74.04

76.81

77.23

77.66

127.50

128.64

128.92

129.93

130.19

133.38

136.15

165.96

THF

Ph

N3

Me

OBz

Ph

N3

Me

OBz

61

1H and 13C NMR spectrum of 9

9 8 7 6 5 4 3 2 1 ppm

-0.000

2.169

5.716

5.736

7.303

7.309

7.317

7.330

7.335

7.340

7.345

7.351

7.359

7.366

7.375

7.384

7.395

7.403

7.407

7.421

7.426

7.441

7.446

7.470

7.475

7.479

7.490

7.499

7.509

7.519

7.523

7.527

7.575

7.593

7.800

7.805

7.812

7.823

7.828

7.832

3.06

1.00

8.50

1.07

2.04

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

27.35

64.10

76.81

77.23

77.65

127.32

128.24

128.75

128.88

129.48

131.96

133.93

136.69

166.51

203.76

THF

Ph

NHBzO

Me

Ph

NHBzO

Me

0dwhuldo (6, iru&khp&rpp 7klv - rsc.org file1 9. nmr data 9-a. nmr spectrum of substrates 1h and 13c...

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