A new method for stereocontrolled synthesis of substituted tetrahydrothiophenes

Journal of the American Chemical Society

Volumn 122, Issue 36, 2000, Pages 8672-8676

  Ponce, Andrés Molina ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 ACYLTETRAHYDROTHIOPHENE; ALDEHYDE; ALKENE; ALLYL ALCOHOL; CARBON; KETONE; TETRAHYDROTHIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CYCLIZATION; ENANTIOMER; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034644407     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001975m     Document Type: Article

References (64)

1. For short reviews, see: (a) Overman, L. E. Aldrichim. Acta 1995, 28, 107-120.
2. (b) Overman, L. E. Ace. Chem. Res. 1992,25, 352-359.
3. Thebtaranonth, C.; Thebtaranonth, Y. Cyclization Reactions; CRC Press: Boca Raton, 1994; pp 29-35.
4. For one illustration, see: Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995,117, 5776-5788.
5. Martinet, P.; Mousset, G. Bull. Soc. Chim. Fr. 1970, 1071-1076.
6. For one illustration, see: MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
7. For a recent commercial synthesis, see: Imwinkelried, R. Chimia 1997, 57, 300-302.
8. (a) Chorghade, M. S.; Gurjar, M. K.; Palakodety, R. K.; Lalitha, S. V. S.; Sadalapure, K.; Adhikari, S. S.; Murugaiah, A. M. S.; Rao, B. V.; Talukdar, A.; Talukdar, A.; Islam, A.; Hariprasad, C.; Rao, A. V. R. Patent Application WO 99-US15050, CAN 132:93203
9. (b) Tsygankova, V. A.; Blume, Ya. B. Biopolim. Kletka 1997,13,484-492.
10. Kato, T.; Tsuzuki, K. Patent Application JP 92-147881, CAN 120:106750.
11. (a) Kim, B. M.; Bae, S. J.; Seomoon, G. Tetrahedron Lett. 1998,39, 6921-6922.
12. (b) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891-6899.
13. Jones, M. F.; Noble, S. A.; Robertson, C. A.; Storer, R. Tetrahedron Lett. 1991, 32, 247-250.
14. Morimoto, Y.; Achiwa, K. Chem. Pharm. Bull. 1987, 35, 3845-3849.
15. (e) Harrold, M. W.; Wallace, R. A.; Farooqui, T.; Wallace, L. J.; Uretsky, N.; Miller, D. D. J. Med. Chem. 1989,32, 874-888.
16. (f) Popsavin, V.; Beric, O.; Velimirovic, S.; Miljkovic, D. J. Serb. Chem. Soc. 1993, 58, 717-719.
17. (g) Aloup, J. C.; Bouchaudon, J.; Farge, D.; James, C.; Deregnaucourt, J.; Hardy-Houis, M. J. Med. Chem. 1987, 30, 24-29.
18. Ohtsuka, T.; Kotaki, H.; Nakayama, N.; Itezono, Y.; Shimma, N.; Kudoh, T.; Kuwahara, T.; Arisawa, M.; Yokose, K.; Seto, H. J. Antibiot. 1993,46, 11-17.
19. Hauptman, E; Shapiro, R.; Marshall, W. Organometallics 1998,17, 4976-4982.
20. (a) For an early review, see: Wolf, E.; Folkers, K. Org. React. 1951, 6, 410-468.
21. For representative recent syntheses, see: (b) Linderman, R. J.; Cutshall, N. S.; Becicka, B. T. Tetrahedron Lett. 1994,35,6639-6642.
22. Eames, J.; Kuhnen, N.; Jones, R. V. H.; Warren, S. Tetrahedron Lett. 1998, 39, 1247-1250.
23. Vlattas, I.; Dellureficio, J.; Cohen, D. S.; Lee, W.; Clarke, F.; Dotson, R.; Mathis, J.; Zoganas, H. Bioorg., Med. Chem. Lett. 1994,4,2067-2072.
24. (e) Brånalt, J.; Kvamström, I.; Svensson, C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994, 59, 4430-4432.
25. (f) Uenishi, J.; Motoyama, M.; Takahashi, K. Tetrahedron: Asymmetry 1994, 5, 101-110.
26. (g) Jones, M. F.; Noble, S. A.; Robertson, C. A.; Store, R. Tetrahedron Lett. 1991,32,247-250.
27. (h) Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Chem. Soc., Chem. Commun. 1991, 741-742.
28. Bredenkamp, M. W.; Holzapfel, C. W.; Swanepoel, A. D. Tetrahedron Lett. 1990,31, 2759-2762.
29. Tetrahydrothiophenes have been made by C-C bond-forming 1,3-dipolar cycloadditions of thiocarbonyl ylides. For representative examples, see: (a) Karlsson, S.; Hogberg, H.-E. Org. Lett. 1999, 1, 1667-1669.
30. (b) Terao, Y.; Aono, M.; Achiwa, K. Heterocydes 1986, 24, 1571-1574.
31. Hojo, M.; Ohkuma, M.; Hosomi, A. Chem. Lett. 1992, 6, 1073-1076.
32. Aono, M.; Terao, Y.; Achiwa, K. Heterocydes 1995, 40, 249-260.
33. (e) Aono, M.; Terao, Y.; Achiwa, K. Heterocydes 1986, 24, 313-315.
34. (a) Johnston, B. D.; Oehlschlager, A. C. Can. J. Chem. 1984, 62, 2148-2154.
35. (b) Overman, L. E.; Kakimoto, M.; Okazaki, M. E.; Meier, G. P. J. Am. Chem. Soc. 1983, 705, 6622-6629.
36. Annis, G. D.; Ley, S. V.; Self, C. R.; Sivaramakrishnan, R. J. Chem. Soc., Perkin Trans, l 1981, 270-277.
37. Eibeck, R. E. Inorg. Synth. 1963, 7, 128-131.
38. Stritjtveen, B.; Kellogg, R. M. J. Org. Chem. 1986, 51, 3664-3671.
39. Facile rearrangement of lia to acyltetrahydrothiophene 13a limited possible condensation conditions.
40. Under no conditions examined was competing formation of 12 minimized significantly.
41. Small amounts (∼5%) of acyltetrahydrothiophenes were formed under these conditions.
42. 1H NMR spectra of the crude reaction product attributable to an acetyl methyl group were seen.
43. Brown, H. C.; Kanner, B. J. Am. Chem. Soc. 1966, 88, 986-987.
44. 3.
45. Overman, L. E.; Rishton, G. M. Organic Syntheses; Wiley: New York, 1998; Collect. Vol. IX; pp 139-142.
46. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
47. (b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
48. For a review of carbon-carbon bond forming reactions of α-thio carbocations, see: Ishibashi, H.; Ikeda, M. Rev. Heteroatom. Chem. 1992, 7, 191-213.
49. 27
50. For reviews, see: (a) Heimgartner, H.; Hansen, H.-J.; Schmid, H. In Iminium Salts in Organic Chemistry; Böhme, H., Viehe, H. G., Eds.; Wiley: New York, 1979; Part 2, pp 655-732.
51. (b) Blechert, S. Synthesis 1989, 2, 71-82.
52. Lolkema, L. D. M.; Semeyn, C.; Ashek, L.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 7129-7140.
53. Jacobsen, E. J.; Levin, J.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4329-4335.
54. (b) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354-5365.
55. For reviews of pinacol rearrangements, see: (a) Bartok, M; Molnar, A. In Chemistry of Ethers, Crown Ethers, Hydroxyl Compounds and Their Sulfur Analogues; Patai, S., Ed.; New York, 1980; Part 2, pp 722-732.
56. (b) Rickbom, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 721-732.
57. This is a reasonable assumption considering the low barriers of C-C single bond rotations: Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A. Confonnalional Analysis; American Chemical Society; Washington, DC, 1965; Chapters 2 and 3.
58. For kinetic studies of the addition of stabilized carbenium ions to alkenes, see: Mayr, H. Angew. Chem. 1990, 29, 1371-1384.
59. For examples of other reactions where the E stereoisomer of α-thio carbenium ions are suggested to react preferentially, see: (a) Mod, I.; Bartlett, P. A.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 709, 7199-7200.
60. (b) Mori, I.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 5966-5977.
61. Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927-8940.
62. 36
63. Gilman, H. J. Organomet. Chem. 1964, 2, 447-454.
64. Metais, E.; Overman, L. E.; Rodriguez, M. I.; Stearns, B. A. J. Org. Chem. 1997, 62, 9210-9216.