− 16 −CSJ Journal Selects Vol. 2
Efficient Synthesis
Reaction Integration Using Electrogenerated Cationic Intermediates
Jun-ichi Yoshida,* Akihiro Shimizu,Yosuke Ashikari, Tatsuya Morofuji,Ryutaro Hayashi, Toshiki Nokami, and Aiichiro NagakiBull. Chem. Soc. Jpn. 2015, 88, 763-775
doi:10.1246/bcsj.20150100
J. Yoshida
S
S
P
R
R
P
S
S
Award Accounts Flow Microreactor System; Electrogenerated Cationic Intermediates
Syntheses and Optical Properties of BODIPY Derivatives Based on Imidazo[1,5-a]pyridine
Jinfa Hu, Yu Li, Yuxiao Wu, Wei Liu,*Yong Wang,* and Yahong Li*Chem. Lett. 2015, 44, 645-647
doi:10.1246/cl.150133
W. Liu
Editor's Choice BODIPY–Pyridine Dyads; Tunable Spectroscopic Properties
Recent Advances in Catalytic Asymmetric C–C Bond-Forming Reactions to
Ketimines Promoted by Metal-Based Catalysts
Naoya Kumagai* and Masakatsu Shibasaki*Bull. Chem. Soc. Jpn. 2015, 88, 503-517
doi:10.1246/bcsj.20140302
M. Shibasaki
Accounts for C–C Bond Formation Catalytic Asymmetric Synthesis; Enantioenriched α-Tertiary Amines
Flash Chemistry Using Trichlorovinyllithium: Switching the Reaction Pathways by High-resolution Reaction Time Control
Aiichiro Nagaki, Yusuke Takahashi, Andrea Henseler, Chika Matsuo, andJun-ichi Yoshida*Chem. Lett. 2015, 44, 214-216
doi:10.1246/cl.140980
J. Yoshida
Cl
Cl
Cl
n-BuLi
Cl Cl
M1
R1
tR1 s
T °C
E1
Cl
ClE1
ClClE1
E1M2 M2
Cl
Cl
Cl
Li
ClLin-BuLi
s-BuLi
E1
E2
E2E1
Editor's Choice Flash Chemistry; Flow Microreactor System
Recent Developments in Organocatalyzed Electroorganic Chemistry
Kelli A. Ogawa and Andrew J. Boydston*Chem. Lett. 2015, 44, 10-16
doi:10.1246/cl.140915
A. J. Boydston
substrate(high Eox)
intermediate(low Eox)
organocatalyst
oxidizedintermediate
anodicoxidation
couplingpartner
product
Highlight Review Organocatalysis; Electroorganic Chemistry
− 17 − CSJ Journal Selects Vol. 2
Catalytic Organic Reactions on the Surface of Silver(I) Oxide in Water
Masaharu Ueno, Arata Tanoue, andShū Kobayashi*Chem. Lett. 2014, 43, 1867-1869
doi:10.1246/cl.140818
S. Kobayashi
OSi
O+
PhH2O, rt
Ag2O (0.01 mol %)PhCHO
Reaction Proceeding on theSurface of Ag2O in Water
>8400 TON !
R
OH
R
Editor's Choice Ag2O-catalyzed Allylation; Water-stable Catalyst
Two-Step, Practical, and Diversity-Oriented Synthesis of Multisubstituted Benzofurans from Phenols through Pummerer Annulation Followed by Cross-coupling
Kei Murakami, Hideki Yorimitsu,* and Atsuhiro OsukaBull. Chem. Soc. Jpn. 2014, 87, 1349-1366
doi:10.1246/bcsj.20140241
OSMe
RRSMe
SMeO
OR"
R
+
OH
Pummerer Annulation/Cross-Coupling Sequence
R' R' R'
Selected Paper Multisubstituted Benzofurans; Pummerer Annulation
H. Yorimitsu
Stimuli-responsive Cooperative Catalysts Based on Dynamic Conformational Changes toward Spatiotemporal Control of Chemical Reactions
Tatsushi Imahori* and Seiji KuriharaChem. Lett. 2014, 43, 1524-1531
doi:10.1246/cl.140680
T. Imahori
Highlight Review Stimuli-responsive Cooperative Catalysts; Dynamic Conformational Changes
Efficient and Versatile Anion Metathesis Reaction for Ionic Liquid Preparation by Using Conjugate Acid and Ortho Ester
Koichiro Takao* and Shinobu TakaoBull. Chem. Soc. Jpn. 2014, 87, 974-981
doi:10.1246/bcsj.20140150 Selected Paper Ionic Liquid Preparation; Ortho Ester
K. Takao
Dynamic Kinetic Resolution of Racemic Allylic Alcohols via Hydrolase–Metal Combo Catalysis: An Effective Method for the Synthesis of Optically Active Compounds
Shuji AkaiChem. Lett. 2014, 43, 746-754
doi:10.1246/cl.140223
S. Akai
Highlight Review Racemic Allylic Alcohols; Hydrolase–Metal Combo Catalysis
− 18 −CSJ Journal Selects Vol. 2
The Chelation-controlled Mukaiyama Aldol Reaction of Chiral α- and β-Alkoxy Aldehydes
Gheorghe-Doru Roiban, Adriana Ilie, and Manfred T. Reetz*Chem. Lett. 2014, 43, 2-10
doi:10.1246/cl.130920
R1
BnO O
H
OSiMe3
R2+
bicoordinate
Lewis acid R1
BnO OHO
R2
bicoordinate
Lewis acidOBn
R1
H
O OSiMe3
R2+
OBn
R1
OH O
R2
Highlight Review Mukaiyama Aldol Reactions; Asymmetric Induction
M. T. Reetz
Development of Synthetic Transformations by Control of Acid-Catalyzed Reactions of Diazocarbonyl Compounds
Takuya Hashimoto* and Keiji Maruoka*Bull. Chem. Soc. Jpn. 2013, 86, 1217-1230
doi:10.1246/bcsj.20130164
COX
N2
X
O
N
N
nucleophilicin acid catalysis
=R R
Award Accounts Diazocarbonyl Compounds; Acid Catalysis
T. Hashimoto
Doyle–Kirmse Reaction Using Triazoles Leading to One-pot Multifunctionalization of Terminal Alkynes
Tomoya Miura,* Takamasa Tanaka, Akira Yada, and Masahiro Murakami*Chem. Lett. 2013, 42, 1308-1310
doi:10.1246/cl.130521
M. Murakami
Editor's Choice Doyle–Kirmse Reaction; One-pot Multifunctionalization
1,3-Dipolar Cycloaddition-based Synthesis of Diverse Heterocyclic Scaffolds
Wei ZhangChem. Lett. 2013, 42, 676-681
doi:10.1246/cl.130504
NH
R1
CO2R
R2
NR3
O
O
R1
N
NHO
OR2
R3
O
R2
N N
O
O R4
N
O
O
N
R1 CO2R
O
OR3
H
R2
R1
R4 R3
[3+2] adductsN
O
ON
R2'
N
O
O
R2
R3 R3'R1
Highlight Review N-Heterocycles; 1,3-Dipolar Cycloaddition
W. Zhang
Facile Synthesis and Lateral π-Expansion of Bisanthenes
Akihito Konishi, Yasukazu Hirao,Kouzou Matsumoto, Hiroyuki Kurata, and Takashi Kubo*Chem. Lett. 2013, 42, 592-594
doi:10.1246/cl.130153
T. Kubo
Direct Cyclization
Scholl reaction
Lateral π-expansion
Diels-Alder reactionDDQ, Sc(OTf)3, acid π
π
Editor's Choice π-Expanded Bisanthenes; Polyperiacenes
− 19 − CSJ Journal Selects Vol. 2
Synergetic Activation of Lipase by an Amino Acid with Alkyl–PEG Sulfate Ionic Liquid
Kazuhide Yoshiyama, Yoshikazu Abe,Shuichi Hayase, Toshiki Nokami, and Toshiyuki Itoh*Chem. Lett. 2013, 42, 663-665
doi:10.1246/cl.130171
T. ItohN
H3C C4H9CH3
SO
OO
OO
C16H3310
IL1
R1
OH L
R2R1
OAc
R2
Vinyl acetate/ i -Pr2O(±)-alcohol (R )-acetate
+Amino acid
Coating material:
Coating material
Lipase protein
N
Editor's Choice Ionic Liquid; Lipase-catalyzed Transesterification
Sequential Peptide Ligation by Combining the Cys–Pro Ester (CPE) and Thioester Methods and Its Application to the Synthesis of Histone H3 Containing a Trimethyl Lysine Residue
Toru Kawakami,* Yuichi Akai, Hisao Fujimoto, Chieko Kita, Yuko Aoki, Takehiko Konishi, Masazumi Waseda, Lisa Takemura, andSaburo Aimoto*Bull. Chem. Soc. Jpn. 2013, 86, 690-697
doi:10.1246/bcsj.20130026
T. Kawakamipeptide A peptide Cpeptide B
peptide B peptide C
NCL
Thioester Method
-CO-CPE Cys-
-CO-CPE -CO-Cys-
peptide A peptide Cpeptide B-CO- -CO-Cys-
BCSJ Award Article Sequential Peptide Ligation; Histone H3 Synthesis
Anthranilamide-masked o-Iodoarylboronic Acids as Coupling Modules for Iterative Synthesis of ortho-Linked Oligoarenes
Masashi Koyanagi, Nils Eichenauer,Hideki Ihara, Takeshi Yamamoto, and Michinori Suginome*Chem. Lett. 2013, 42, 541-543
doi:10.1246/cl.130136
M. Suginome
oligo(o -arene)s"coupling module"
orthosilylation
iododesilylation
IClHN NH
O
B
B(aam)
B(aam)
H
B(aam)
B(aam)
I
B(aam)
R
[Ru]
iterativecoupling
R
R
R3
R1
R2
R4
SiR'3
Editor's Choice ortho-Linked Oligoarenes; Suzuki–Miyaura Coupling
Synthesis of High-molecular-weight Head-to-tail-type Poly(3-substituted-thiophene)s by Cross-coupling Polycondensation with [CpNiCl(NHC)] as a Catalyst
Shunsuke Tamba, Kanta Fuji, Hikaru Meguro, Shuji Okamoto, Tadashi Tendo,Ryo Komobuchi, Atsushi Sugie,Takashi Nishino, and Atsunori Mori*Chem. Lett. 2013, 42, 281-283
doi:10.1246/cl.2013.281
A. Mori
SH Br
nHex
TMPMgCl·LiCl
S
nHex 74%,Mw=815000Mw/Mn=3.49
n
NN
iPr iPr
iPr iPrNiCl
[CpNiCl(SIPr)]
Self-standing P3HT film
Editor's Choice Polythiophene; NHC–Ni Catalyst