CHEMISTRY 534 PERICYCLIC REACTIONS FALL 2013 I. General A. W. Carruthers, Cycloaddition Reactions in Organic Synthesis; Pergamon Press, 1990 B. I. Fleming, Frontier Orbitals and Organic Chemical Reactions; Wiley, 1976; Ch 4 C. I. Fleming, Molecular Orbitals and Organic Chemical Reactions; Wiley, 2009; Ch 6 D. N. T. Ahn, “Frontier Orbitals: A Practical Manual”, Wiley, 2007. E. R. B. Woodward, R. Hoffman, The Conservation of Orbital Symmetry; Verlag Chemie, 1971 F. G. Desimoni, G. Tacconi, A. Barco, G. Pollini, Natural Product Synthesis through Pericyclic

Reactions; American Chemical Society, 1983; Monograph 180 G. Pericyclic Reactions; Vols. I and II; A. P. Marchand and R. E. Lehr, Eds.; Academic Press,

1977 H. Comprehensive Organic Synthesis Vol 5. Combining C-C π Bonds; L. A. Paquette, Ed.;

Pergamon Press, 1991. This entire volume (>1200 pages) is dedicated to pericyclic reactions.

I. F. Fringuelli and A. Taticchi Dienes in the Diels Alder Reaction; Wiley-Interscience, 1990 J. Metal Catalyzed Cycloaddition Reactions in Organic Synthesis; S. Kobayashi, K. A. Jørgensen,

Eds.; Wiley-VCH, 2002 II. Cycloadditions A. [4+2] 1. General a. Org. React. 1948, 4, 1; Ibid. 1948, 4, 60; Ibid. 1949, 5, 136 b. J. Sauer, Angew. Chem., Int. Ed. Engl. 1962, 1, 269 c. J. Sauer, R. Sustmann, Angew. Chem., Int. Ed. Engl. 1980, 19, 779 d. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem.,

Int. Ed., 2002, 1669. 2. Stereochemistry a. R. K. Hill, J. G. Martin, Chem. Rev. 1961, 61, 537 b. J. Sauer, Angew. Chem., Int. Ed. Engl. 1967, 6, 16 c. J. A. Berson, Acc. Chem. Res. 1972, 5, 105 3. Heteroatomic a. J. Hamer, 1,4-Cycloaddition Reactions; Academic Press, 1967 b. D. Boger, S. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis; Academic

Press, 1987 c. G. Desimoni, G. Tacconi, Chem. Rev. 1975, 75, 651 d. R. R. Schmidt, Angew. Chem., Int. Ed. Engl. 1973, 13, 212 e. G. Kirby, Chem. Soc. Rev. 1977, 6, 1 f. M. Petrizilka, J. Grayson, Synthesis 1981, 753 g. S. Weinreb, Acc. Chem. Res. 1985, 18, 16 h. S. Danishefsky, Acc. Chem. Res. 1981, 14, 400 i. L. Tietze in Selectivity - A Goal for Synthetic Efficiency; W. Bartmann, B. Trost, Eds.;

Verlag Chemie, 1984 j. R. R. Schmidt, Acc. Chem. Res. 1986, 19, 250 4. Intramolecular a. G. Brieger, J. Bennett, Chem. Rev. 1980, 80, 63 b. T. Kametani, Tetrahedron 1981, 37, 3 c. W. Oppolzer, Synthesis 1978, 793 d. W. Oppolzer, Heterocycles 1980, 14, 1615 e. R. L. Funk, K. P. C. Vollhardt, Chem. Soc. Rev. 1980, 9, 41 f. A. Fallis, Can. J. Chem. 1984, 62, 183 g. E. Ciganek, Org. React. 1984, 32, 1 h. D. Craig, Chem. Soc. Rev. 1987, 16, 187 i. D. F. Taber, Intramolecular Diels-Alder and Ene Reactions; Springer-Verlag, 1984

j. W. R. Roush in Advances in Cycloaddition, Vol. 2; D. P. Curran, Ed.; JAI Press, 1990; pp 91-146

2

k. A. Fallis, Acc. Chem. Res. 1999, 32, 464. 5. Lewis-Acid Catalysis a. P. Eaton, J. Am. Chem. Soc. 1960, 82, 4436 b. K. N. Houk, J. Am. Chem. Soc. 1973, 95, 4094 c. W. R. Roush, J. Org. Chem. 1980, 45, 4267 d. K. Houk, J. Am. Chem. Soc. 1987, 109, 14; Ibid, 1990, 112, 4127 e. H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310 f. K. Narasaka Synthesis 1991, 1 g. H. B. Kagan, O. Riant Chem. Rev. 1992, 92, 1007 h. U. Pindur et. al. Chem. Rev. 1993,93, 741 i. L. Deloux, M Srebnik. Chem. Rev. 1993, 93, 785 6. Under Pressure a. W. LeNoble, Chem. Rev. 1978, 78, 207 b. W. G. Dauben, J. Am. Chem. Soc. 1980, 102, 6893 7. Aqueous/Lithium Perchlorate a. P. Grieco, Tetrahedron 1986, 42, 2847 b. R. Breslow, Tetrahedron Lett. 1984, 25, 1239 c. W. L. Jorgensen et al. J. Am. Chem. Soc. 1991, 113, 7430 8. Retrocycloaddition a. B. Rickborn, Org. React. 1998, 52, 1; Ibid. 1998, 53, 223 B. [3+2] 1. General a. R. Huisgen, Chemistry of Alkenes; S. Patai, Ed.; Wiley, 1964, pp 806-877 b. 1,3-Cycloaddition Chemistry; A. Padwa, Ed.; Wiley, 1984; Vols. 1 and 2 c. J. J. Tufariello, Acc. Chem. Res. 1979, 12, 396 d. R. Huisgen, Angew. Chem., Int. Ed. Engl. 1963, 2, 565, 633 e. D. S. C. Black, Synthesis 1975, 205 f. Advances in Cycloadditions; D. P. Curran, Ed.; JAI Press, 1988 g. K. B. G. Torrsell, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH,

1988 h. A. Padwa and A. M. Schoffstall in Advances in Cycloaddition, Vol. 2; D. P. Curran,

Ed.; JAI Press, 1990; pp 1-90 i. B. M. Trost "[3+2] Cycloadditions with Trimethylenemethane Equivalents" Angew.

Chem. Int. Ed. Engl. 1986, 25, 1 j. E. Vedejs "Generation of Ylides by Desilation", Chem. Rev. 1986, 86, 941 k. D. L. Boger and C. Brotherton in Advances in Cycloaddition Vol. 2; D. P. Curran, Ed.;

JAI Press, 1990; pp 147-219 l. The Chemistry of Heterocyclic Compounds: Synthetic Applications of 1,3-Dipolar

Cycloaddition Chemistry Toward Heterocycles and Natural Products, Padwa, A.; Pearson, W. H., Eds.; Wiley-Interscience: New York, 2002

2. Intramolecular a. W. Oppolzer, Angew. Chem., Int. Ed. Engl. 1977, 16, 10 b. 1,3-Cycloaddition Chemistry; A. Padwa, Ed.; Wiley, 1984; Vol. 2, Ch 12 c. P. Confalone, Org. React. 1988, 36, 1 C. [2+2] 1. Photochemical a. S. Baldwin in Organic Photochemistry; A. Padwa, Ed.; Marcel Dekker, 1981; Vol. 5 b. P. DeMayo, Acc. Chem. Res. 1971, 4, 41 c. M. T. Crimmins, Chem. Rev. 1988, 88, 1453 d. M. T. Crimmins, Org. React. 1993, 44, 29.7 2. Thermal a. R. Huisgen, Acc. Chem. Res. 1977, 10, 117, 199 b. B. Snider, Chem. Rev. 1988, 88, 793 c. B. Ernst et al. Angew. Chem. Int. Ed. Engl. 1988, 27, 797 d. L. Ghosez and M. J. O'Donnell in Pericyclic Reactions, Vol. 2; A. P. Marchand and R.

E. Lehr, Eds.; Academic Press, 1977; pp 79-140 e. J. A. Hyatt and R. W. Reynolds, Org. React. 1994, 45, 159 D. [2+1]

3

1. General a. M. Jones, R. A. Moss, Carbenes; J. Wiley, 1973 b. N. Kirmse, Carbene Chemistry; Academic Press, 1971 c. D. S. Wulfman, B. Poling in Reactive Intermediates; R. A. Abramovich, Ed.; Plenum,

1980; Vol. 1, p 321 d. T. Tsuji and S. Nishida, "Preparation of Cyclopropyl Compounds" in The Chemistry of

the Cyclopropyl Group, Part I, S. Patai, Ed., pp 307-373 e. H. U. Ressig, "Organic Synthesis via Cyclopropanes", Ibid., pp 375-403 f. J. Salaün, Chem. Rev. 1989, 89, 1247 g. J. Salaün and M. Baird, Current Medicinal Chemistry, 1995, 2, 511 h. W. Donaldson, Tetrahedron 2001, 57, 8589 i. S. E. Denmark in “Cycloaddition Reactions in Organic Synthesis”; K. Jorgensen and

S. Kobayashi, Eds. Wiley-VCH, 2002; Chapt. 3. 2. From Diazo Compounds a. V. Dare, Org. React. 1970, 18, 217; H. Davies, Org. React. 2001, 57, 1 b. R. A. Butler, Organic Reaction Mechanisms; Interscience, 1973; p 203 c. M. P. Doyle, Chem Rev. 1986, 56, 919; Chem. Rev. 1998, 98, 911 d. G. Maas, Topics in Current Chemistry 1987, 137, 75 e. A. Pfaltz, Accounts Chem Res. 1993, 26, 339 f. M. Doyle, M. McKervey, and T. Ye, Modern Catalytic Methods for Organic Synthesis

with Diazo Compounds; Wiley; 1998 3. From Zinc Carbenoids a. H. E. Simmons, Org. React. 1973, 20, 1 b. A. Charette, Org. React. 2001, 58, 1 4. Intramolecular a. Org. React. 1979, 26, 361 E. Higher Order 1. General a. P. A. Wender et al. in “Comprehensive Organometallic Chemistry III”, Pergamon Press:

Oxford, Chapter 10.13. 2. [4+3] a. M. A. Harmata, Acc. Chem. Res. 2001, 595 b. M. A. Harmata, Adv. Synth. Catal. 2006, 2297 3. [5+2] a. P. A. Wender, In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Samford,

CT, 1999; pp 1–45 4. [6+4] a. J. H. Rigby, Org. React. 1997, 49, 331; Ibid. 1997, 51, 351 F. Asymmetric Cycloadditions 1. General a. L. Paquette in Asymmetric Synthesis; J. D. Morrison, Ed.; Academic Press, 1984; Vol.

3, p 455 b. W. Oppolzer, Angew. Chem., Int. Ed. Engl. 1984, 23, 876 2. Diels-Alder Reaction a. G. Helmchen in Modern Synthetic Methods; R. Scheffold, Ed.; Springer Verlag, 1986;

Vol. 4, pp 262-306 b. M. J. Taschner in Organic Synthesis: Theory and Applications; T. Hudlicky, Ed. JAI

Press, 1989. pp 1-101 c. D. A. Evans and J. S. Johnson in Comprehensive Asymmetric Catalysis; E. N.

Jacobsen, A. Pfaltz, H. Yamamoto, Eds.; Springer-Verlag, 1999; Ch 33.1 d. D. A. Evans and J. S. Johnson, Acc. Chem. Res. 2000, 325 e. T. Ooi and K. Maruoka in Comprehensive Asymmetric Catalysis; E. N. Jacobsen, A.

Pfaltz, H. Yamamoto, Eds.; Springer-Verlag, 1999; Ch 33.2 f. K. Maruoka in Catalytic Asymmetric Synthesis, 2nd Ed.; I. Ojima, Ed.; Wiley, 2000; Ch

8A 3. [3+2] Cycloadditions a. H. Pellisier, Tetrahedron 2007, 63, 3235 b. S. Kanemasa, Synthesis 2001, 1371

4

c. K. V. Gothelf In “Cycloaddition Reactions in Organic Synthesis”; K. Jorgensen and S. Kobayashi, Eds. Wiley-VCH, 2002; Chapt. 6.

d. S. Kanemasa, In “Cycloaddition Reactions in Organic Synthesis”; K. Jorgensen and S. Kobayashi, Eds. Wiley-VCH, 2002; Chapt. 7

4. Chiral Lewis Acids a. K. Koga et al. J. Chem. Soc. Chem. Commun. 1979, 432 b. K. Maruoka and H. Yamamoto in Catalytic Asymmetric Synthesis; I. Ojima, Ed.; Wiley,

1993; Ch 9 c. Y. Hayashi in Cycloaddition Reactions in Organic Synthesis; S. Kobayashi, K. A.

Jørgensen, Eds.; Wiley-VCH, 2002; Ch 1 III. Ene Reactions A. Intermolecular 1. H. M. R. Hoffmann, Angew. Chem., Int. Ed. Engl. 1969, 8, 556 2. B. Snider, Acc. Chem. Res. 1980, 13, 426 3. K. Mikami, Chem. Rev. 1992, 92, 1021. B. Intramolecular 1. W. Oppolzer, Angew. Chem., Int. Ed. Engl. 1978, 17, 476 2. W. Oppolzer, Angew. Chem., Int. Ed. Engl. 1989, 28, 38 C. Asymmetric 1. K. Mikami and M. Tereda in Comprehensive Asymmetric Catalysis; E. N. Jacobsen, A.

Pfaltz, H. Yamamoto, Eds.; Springer-Verlag, 1999; Ch 32 IV. Sigmatropic Rearrangements A. [3,3]-Rearrangements 1. Claisen Rearrangements a. P. Wipf, In Comprehensive Organic Synthesis, L. Paquette, Ed.; Pergamon, 1991; Vol.

5; Ch 7.2. b. F. E. Ziegler, Chem. Rev. 1988, 88, 1423. c. S. Blechert, Synthesis 1989, 71. d. R. P. Lutz, Chem. Rev. 1984, 84, 205. e. R. K. Hill In Asymmetric Synthesis, J. D. Morrison, Ed.; Academic Press, 1984; Vol. 3;

p. 503. f. C. J. Moody, Adv. Heterocyclic Chem. 1987, 42, 203. g. A. M. Castro, Chem. Rev. 2004, 104, 2939 h. The Claisen Rearrangement, M. Hiersemann, U. Nubbemeyer, Eds. Wiley-VCH, 2007. 2. Cope, Oxy-Cope, Anionic Oxy-Cope a. R. K. Hill In Comprehensive Organic Synthesis, L. Paquette, Ed.; Pergamon, 1991; Vol.

5; Ch 7.1. b. S. J. Rhoads, N. Raulins, Org. React. 1975, 22, 1. c. L. Paquette, Angew. Chem. Inter Ed. Engl. 1990, 29, 609. d. F. E. Ziegler In Comprehensive Organic Synthesis, L. Paquette, Ed.; Pergamon, 1991:

Vol. 5; Ch 7.3. e. S. R. Wilson, Org. React. 1993, 43, Ch 2. B. [2,3]-Rearrangements 1. General: R. Brückner, In Comprehensive Organic Synthesis, E. Winterfeldt, Ed.;

Pergamon, 1991; Vol. 6; Ch 4.6. 2. Wittig Rearrangement a. J. A. Marshall, In Comprehensive Organic Synthesis, G. Pattenden, Ed.; Pergamon,

1991; Vol. 3; Ch 3.11. b. R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 1979, 18, 563. c. T. Nakai, K. Mikami, Chem. Rev. 1986, 86, 885. 3. Stevens Rearrangement a. I. Markó, In Comprehensive Organic Synthesis, G. Pattenden, Ed.; Pergamon, 1991;

Vol. 3; Ch 3.10. b. S. H. Pine, Org. React. 1970, 18, Ch 4. c. E. Vedejs, Accounts Chem. Res. 1984, 17, 358. 4. Evans-Mislow Rearrangement

5

a. D. A. Evans, G. C. Andrews, Accounts Chem. Res. 1974, 7, 147. C. [1,3]-Rearrangements 1. Vinyl Cyclopropane Rearrangements a. T. Hudlicky, J. W. Reed, In Comprehensive Org. Synthesis, L. Paquette, Ed.;

Pergamon, 1991; Vol. 5; Ch 8.1. b. T. Hudlicky, T. M. Kutchan, S. M. Naqvi, Org. React. 1985, 33, 247. c. H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev.

1989, 89, 165. d. B. M. Trost, Top. Curr. Chem. 1986, 133, 3.