Allyl sulfones as precursors to allylzincs in the palladium-catalyzed zinc-ene cyclization: Highly efficient synthesis of enantiopure (-)-erythrodiene

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3637-3640

  Deng, Kai ^a   Chalker, Justin ^a   Yang, Ao ^a   Cohen, Theodore ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ERYTHRODIENE; PALLADIUM; SPIRO COMPOUND; SULFONE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM; SPIRO COMPOUNDS; STEREOISOMERISM; SULFONES; ZINC;

EID: 24044438851     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051049i     Document Type: Article

References (55)

1. (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38-52.
2. (b) Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941-1948.
3. (c) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, pp 29-61.
4. Cheng, D.; Zhu, S.; Liu, X.; Norton, S. H.; Cohen, T. J. Am. Chem. Soc. 1999, 121, 10241-10242.
5. Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412-13.
6. Intermolecular comparisons: Lehmkuhl, H.; Reinehr, D.; Hennenberg, D.; Schomburg, G.; Schroth, G. Ann. Chem. 1975, 119-144.
7. Lehmkuhl, H.; Nehl, H. J. Organomet. Chem. 1973, 60, 1-10.
8. Lehmkuhl, H.; Doring, I.; Nehl, H. J. Organomet. Chem. 1981, 221, 123-130.
9. Intramolecular comparisons: Courtemanche, G.; Normant, J.-F. Tetrahedron Lett. 1991, 32, 5317-5320.
10. Meyer, C.; Marek, I.; Normant, J.-F.; Platzer, N. Tetrahedron Lett. 1994, 35, 5645-5648.
11. Lorthiois, E.; Marek, I.; Meyer, C.; Normant, J.-F. Tetrahedron Lett. 1995, 36, 1263-1266.
12. Lorthiois, E.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 89-92.
13. Review: Knochel, P.; Perea, J. J. A.; Jones, P. Tetrahedron 1998, 54, 8275-8319.
14. (a) Oppolzer, W.; Schröder, F. Tetrahedron Lett. 1994, 35, 7939-7942.
15. 4; Yasui, K.; Goto, Y.; Yajima, T.; Taniseki, Y.; Fugami, K.; Tanaka, A.; Tamaru, T. Tetrahedron Lett. 1993, 34, 7619-7622.
16. Hawthorne, D. G.; Johns, S. R.; Willing, R. I. Aust. J. Chem. 1976, 29, 315-326.
17. 7 we consider that there is considerable uncertainty about the stereochemistry and even the mechanism of the Pd-catalyzed Zn-ene cyclization; see below.
18. Trost, B. M.; Schmuff, N. R.; Miller, M. J. J. Am. Chem. Soc. 1980, 102, 5979-5981.
19. Clayden, J.; Julia, M. J. Chem. Soc., Chem. Commun. 1994, 1905-1906.
20. (a) Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon: New York, 1993; pp 106, 116.
21. (b) Kocienski, P. J. Tetrahedron Lett. 1979, 20, 441-442.
22. (c) Phillips, E. D.; Warren, E. S.; Whitham, G. H. Tetrahedron 1997, 53, 307-320.
23. (d) Savoia, D.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Perkin Trans. 1 1977, 123-125.
24. Trost, B. M.; Schmuff, N. R. J. Am. Chem. Soc. 1985, 107, 396-405.
25. Liu, C. Q.; Kudo, K.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1996, 61, 494-502.
26. Limitations of this cyclization procedure became evident when attempts to cyclize the analogues of 3 bearing methyl groups on either terminus of the nonallylic alkene were unsuccessful. It is conceivable that special reaction conditions such as those required in a literature synthesis of (-)-erythrodiene (see below) would be successful. Other conditions were not tried.
27. For examples, see: (a) Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208-1213.
28. (b) Giese, B.; Mazundar, P. Chem. Ber. 1981, 114, 2859-2865.
29. (c) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655-1659.
30. (d) Binns, M. R.; Haynes, R. K.; Lambert, D. E.; Schober, P. A. Tetrahedron Lett. 1985, 26, 3385-3388.
31. (e) Guo, B.-S.; Doubleday, W.; Cohen, T. J. Am. Chem. Soc. 1987, 109, 4710-4711.
32. (f) Hannaby, M.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1989, 303-311.
33. (g) Sato, T.; Hiramura, Y.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1989, 30, 2821-2824.
34. (h) Behrens, K.; Kneisel, B. O.; Noltemeyer, M.; Bruckner, R. Liebigs Ann. Chem. 1995, 385-400.
35. (i) Wang, X. Z.; Wu, Y. L.; Jiang, S. D.; Singh, G. Tetrahedron Lett. 1999, 40, 8911-8914.
36. Cohen, T.; Guo, B. S. Tetrahedron 1986, 42, 2803-2808.
37. (a) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 1287-1290.
38. (b) Bortolini, O.; Di Furia, F.; Modena, G.; Seraglia, R. J. Org. Chem. 1985, 50, 2688-2690.
39. (c) Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chem. Soc. 1999, 121, 4924-4925.
40. (d) Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X. Q.; Noyori, R. Tetrahedron 2001, 57, 2469-2476.
41. (e) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772-10773.
42. (f) Choudary, B. M.; Reddy, C. R. V.; Prakash, B. V.; Kantam, M. L.; Sreedhar, B. J. Chem. Soc., Chem. Commun. 2003, 754-755.
43. Gais, H. J.; Gumpel, M. V.; Raabe, G.; Mueller, J.; Braun, S.; Lindner, H. J.; Rohs, S.; Runsink, J. Eur. J. Org. Chem. 1999, 7, 1627-1652.
44. Padwa, A.; Kamigata, N. J. Am. Chem. Soc. 1977, 99, 1871-1880. The use of 1-bromo-4-pentene as an alternative electrophile provided no desired product under the same reaction conditions.
45. Stereochemistry is assumed on the basis of the results in Scheme 3 and the reported structures of all other kinetic products of metallo-ene cyclizations using main group organometallics.
46. Pathirana, C.; Fenical, W.; Corcoran, E.; Clardy, J. Tetrahedron Lett. 1993, 34, 3371-3372.
47. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773-2779.
48. Oppolzer, W.; Flachsmann, F. Helv. Chim. Acta 2001, 84, 416-430.
49. Hua, D. H.; Venkaraman, S.; Ostrander, R. A.; Sinai, G. Z.; McCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507-515.
50. Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147-155.
51. The largely 1,2-addition of a secondary amine to 2-phenylsulfonyl-1,3- butadiene has been reported: Bäckvall, J.-E.; Juntunen, S. K. J. Am. Chem. Soc. 1987, 109, 6396-6403.
52. Bäckvall, J. E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850-5851.
53. Kemp, M. I.; Whitby, R. J.; Coote, S. J. Synthesis 1998, 557-568.
54. 6a Corresponding allylmagnesium intermediates give only elimination: Oppolzer, W.; Gaudin, J.-M.; Bedoya-Zurita, M.; Hueso-Rodriguez, J.; Robyr, C. Tetrahedron Lett. 1988, 29, 4709-4712.
55. Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470 and reference therein.