Chiral bicyclic lactams: useful precursors and templates for asymmetric syntheses1

Abstract

A survey of the utilitarian bicyclic lactams is presented. These chiral templates have provided, and continue to provide, access to a plethora of natural and unnatural carbocyclic products in high enantiomeric purity. Their synthetic versatility has recently grown with the development of new methods for the construction of heterocycles. In addition to the cyclopentenone, cyclohexenone and hexahydroindenone systems, products derived from bicyclic lactams now include optically active piperidines, pyrrolidines, pyrrolidinones and tetrahydroisoquinolines. These favourable properties make the bicyclic lactams highly adaptable tools for asymmetric synthesis.

References

1. For a recent authoratative review on asymmetric syntheses see: Houben-Weyl, Methods of Organic Chemistry, Vols. E21: Stereoselective Synthesis, ed. G. Helmchen, R. W. Hoffman, J. Mulzer and E. Schaumann, Georg Thieme Verlag 1995; Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, Orlando, 1983–1985.
2. (a) D. Romo and A. I. Meyers, Tetrahedron, 1991, 47, 9503; (b) D. Romo and A. I. Meyers, J. Org. Chem., 1992, 57, 6265; (c) A. I. Meyers and L. J. Westrum, Tetrahedron Lett., 1993, 34, 7701; (d) A. I. Meyers, in Stereocontrolled Organic Synthesis, ed. B. M. Trost, Blackwell Scientific Publications, 1994, pp. 145–161; (e) J. E. Resek and A. I. Meyers, Synlett, 1995, 145; (f) M. Es-Sayed, P. Devine, L. E. Burgess, A. de Meijere and A. I. Meyers, J. Chem. Soc., Chem. Commun., 1995, 141; (g) C. J. Andres, N. Spetseris, J. R. Norton and A. I. Meyers, Tetrahedron Lett., 1995, 36, 1613; (h) J. B. Schwarz and A. I. Meyers, J. Org. Chem., 1995, 60, 6511; (i) for other reports on the use of these bicyclic lactams see, J. A. Ragan and M. C. Claffey, Heterocycles, 1995, 41, 57; (j) T. Wunsch and A. I. Meyers, J. Org. Chem., 1990, 55, 4233.
3. M. Tsuda, M. Ishibashi, K. Agemi, T. Sasaki and J. Kobayashi, Tetrahedron, 1991, 47, 2181; B. R. Gaikwad, T. Mayelvaganan, B. A. Vyas and S. V. Bhat, Phytochemistry, 1990, 29, 3963.
4. A. I. Meyers and L. Snyder, Synlett, 1991, 863; L. Snyder and A. I. Meyers, J. Org. Chem., 1993, 58, 7507 and references cited therein.
5. D. A. Sandham and A. I. Meyers, J. Chem. Soc., Chem. Commun., 1995, 2511 and references cited therein for previous syntheses of Magellanine.
6. P. N. Devine and A. I. Meyers, J. Am. Chem. Soc., 1994, 116, 2633.
7. For other routes to enantiomerically pure vicinal quaternary tertiary stereocenters see: M. Yamaguchi, M. Hamada, H. Nakashima and T. Minami, Tetrahedron Lett., 1987, 28, 1785; H.-J. Knölker and R. Graf, Tetrahedron Lett., 1993, 34, 4765.
8. For a recent enantioselective (41% ee) synthesis of trichodiene see: J. C. Gilbert and R. D. Selliah, J. Org. Chem., 1993, 58, 6255.
9. G. Lajoie, F. Lepine, L. Maziak and B. Belleau, Tetrahedron Lett., 1983, 24, 3815.
10. For a review, see P. Metzner, Synthesis, 1992, 1185; Y. Tamaru, T. Harada and Z.-I. Yoshida, J. Am. Chem. Soc., 1980, 102, 2392 and references cited therein.
11. (a) L. E. Burgess and A. I. Meyers, J. Org. Chem., 1992, 57, 1656 and references cited therein; (b) A. D. Elbein and R. Molyneux, in Alkaloids; Chemical and Biological Perspectives, ed. S. W. Pelletier, 1987, vol. 57, p. 1; (c) M. J. Munchhof and A. I. Meyers, J. Am. Chem. Soc., 1995, 117, 5399 and references cited therein; (d) T. Mukaiyama and M. Asami, Top. Curr. Chem., 1985, 127, 133.
12. L. J. Westrum and A. I. Meyers, Tetrahedron Lett., 1994, 35, 973 for other syntheses of chiral 3-substituted pyrrolidines see S. E. Denmark and L. R. Marcin, J. Org. Chem., 1995, 60, 3221.
13. A. Jossang, A. Melhaoui and B. Bodo, Heterocycles, 1996, 43, 755.
14. (a) M. A. Tschantz, L. E. Burgess and A. I. Meyers, Org. Synth., 1995, 73, 221; (b) for other syntheses of 5-pyrrolidinones, see Z.-Y. Wei and E. E. Knaus, Tetrahedron Lett., 1993, 34, 4439; (c) for other syntheses of 2-pyrrolidines, see H. Suzuki, S. Aoyagi and C. Kibayashi, Tetrahedron Lett., 1994, 35, 6119.
15. K. Ishihara, A. Mori and H. Yamamoto, Tetrahedron, 1990, 46, 4595; I. Mori, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett and C. H. Heathcock, J. Org. Chem., 1990, 55, 6107; A. Alexakis and P. Mangeney, Tetrahedron: Asymmetry, 1990, 1, 477.
16. (a) A. I. Meyers and L. E. Burgess, J. Org. Chem., 1991, 56, 2294; (b) L. E. Burgess and A. I. Meyers, J. Am. Chem. Soc., 1991, 113, 9858.
17. (a) B. J. Newhouse, A. I. Meyers, N. S. Sirisoma, M. P. Braun and C. R. Johnson, Synlett, 1993, 573; (b) J. E. Resek and A. I. Meyers, Tetrahedron Lett., 1995, 36, 7051.
18. (a) A. I. Meyers and L. Snyder, J. Org. Chem., 1992, 57, 3814; (b) A. I. Meyers and L. Snyder, J. Org. Chem., 1993, 58, 36; (c) for a recent synthesis of cis-2, 3-disubstituted pyrrolidines, see T. Kercher and T. Livinghouse, J. Am. Chem. Soc., 1996, 118, 4200.
19. (a) C. J. Andres, P. H. Lee, T. H. Nguyen and A. I. Meyers, J. Org. Chem., 1995, 60, 3189 and references cited therein; (b) C. J. Andres and A. I. Meyers, Tetrahedron Lett., 1995, 36, 3491 and references cited therein; (c) for recent syntheses of aminopyrolidines see G. M. Taylor, S. J. Baker, A. Gedney, D. J. Pearson and G. E. M. Sibley, Tetrahedron Lett., 1996, 37, 1297; (d) U. Chiacchio, F. Casuscelli, A. Corsaro, V. Librando, A. Rescifina, R. Romeo and G. Romeo, Tetrahedron, 1995, 51, 5689.
20. (a) A. I. Meyers, M. A. Tschantz and G. P. Brengel, J. Org. Chem., 1995, 60, 4359; (b) G. P. Brengel, C. Rithner and A. I. Meyers, J. Org. Chem., 1994, 59, 5144.
21. H.-J. Knölker and R. Graf, Tetrahedron Lett., 1993, 34, 4765 and references cited therein.
22. G. P. Brengel and A. I. Meyers, J. Org. Chem., 1996, 61, 3230 see also I. Fleming, Chemtracts: Org. Chem., 1996, 9, 1.
23. (a) A. I. Meyers, C. J. Andres, J. E. Resek, M. A. McLaughlin, C. C. Woodall and P. H. Lee, J. Org. Chem., 1996, 61, 2586 and references cited therein; (b) for other syntheses of hydroxypyrrolidines see J. C. Carretero, R. G. Arrayás and I. S. de Gracia, Tetrahedron Lett., 1996, 37, 3379; (c) I. Burley and A. T. Hewson, Tetrahedron Lett., 1994, 35, 7099.
24. A. H. Fray and A. I. Meyers, Tetrahedron Lett., 1992, 33, 3575; A. H. Fray and A. I. Meyers, J. Org. Chem., 1996, 61, 3362.
25. A. Padwa and W. Dent, J. Org. Chem., 1987, 52, 235.
26. For the syntheses of (±)-conessine the related (±)-conanine ring system, see G. Stork, S. D. Darling, I. T. Harrison and P. S. Wharton, J. Am. Chem. Soc., 1962, 84, 2018; M. Mukherjee and L. M. Mukherjee, Indian J. Chem., 1981, 20B, 1019 and references cited therein.
27. M. Kopach, A. H. Fray and A. I. Meyers, J. Am. Chem. Soc., 1996, 118, 9876.
28. (a) For a recent asymmetric synthesis of 2, 3-disubstituted piperidines via chiral lactams, see L. Micouin, J.-C. Quirion and H.-P. Husson, Tetrahedron Lett., 1996, 37, 849; (b) M. J. Munchhof and A. I. Meyers, J. Org. Chem., 1995, 60, 7084; (c) for an asymmetric synthesis of (–)-coniine via chiral bicyclic lactam 62(R¹= H), see M. Amat, N. Llor and J. Bosch, Tetrahedron Lett., 1994, 35, 2223.
29. (a) M. J. Munchhof and A. I. Meyers, J. Org. Chem., 1995, 60, 7086 and references cited therein; (b) M. J. Munchhof and A. I. Meyers, J. Org. Chem., 1996, 61 in the press; (c) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1996, 118, 4916.
30. A. Eschenmoser, Pure Appl. Chem., 1973, 33, 69.
31. For a recent asymmetric synthesis of (–)-dihydropinidine via angular hydrogen bicyclic lactam 62(R¹= H), see M. Amat, N. Llor, J. Hidalgo, A. Hernández and J. Bosch, Tetrahedron: Asymmetry, 1996, 7, 977.