Double-stereodifferentiating crotylation reactions with chiral (E)-crotylsilanes. Evaluation of a new approach for the synthesis of polypropionate-derived natural products

Journal of the American Chemical Society

Volumn 118, Issue 49, 1996, Pages 12475-12476

  Jain, Nareshkumar F ^a   Takenaka, Norito ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROPIONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030457121     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962877x     Document Type: Article

References (28)

1. (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
2. (b) Roush, W. R. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1-53.
3. Fleming, I. Chem. Soc. Rev. 1981, 10, 83-99.
4. Staunton, J. Angen: Chem., Int. Ed. Engl. 1991, 30, 1302-1306
5. (a) Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503-7509.
6. (b) German, C. In Comprehensive Organic Synthesis: Additions to C-X x-Bonds Part 2; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Chapter 2.4.
7. (a) Panek, J. S.; Beresis, R. T. J. Org. Chem. 1993, 58, 809-811.
8. (b) Jain, N. F.; Cirillo, P. F.; Pelletier, R.; Panek, J. S. Tetrahedron Lett. 1995, 36, 8727-8730.
9. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343.
10. (a) Jain, N. F.; Cirillo, P. F.; Schaus, J. V.; Panek, J. S. Tetrahedron Lett. 1995, 36, 8723-8726.
11. (b) Panek, J. S.; Yang, M. G.; Solomon, J. J. Org. Chem. 1993, 58, 1003-1010.
12. (a) Ireland, R. E.; Thaisrivongs, S.; Dussault, P. H. J. Am. Chem. Soc. 1988, 110, 5768-5779.
13. (b) Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1988, 48, 5180-5184.
14. The relative and absolute stereochemistry of all crotylation products was assigned through the measurement of a three-bond coupling constant of corresponding six-member acetonide (see Supporting Information for details). For example, see: Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316 and references therein.
15. In a related unpublished example (eq 1) that bears relevance to homoallylic alcohol 4, we have documented that the reaction of aldehyde 7e with (5)-l produces 5,6-anti-6,7-anti homoallylic alcohol 25. matrix chemical equation
16. (a) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748-2755.
17. (b) Reetz, M. T. Ace. Chem. Res. 1993, 26, 462-468.
18. (a) Panek, J. S.; Cirillo, P. F. J. Org. Chem. 1993, 58, 294-296.
19. (b) Mikami, K.; Kawamoto, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1161-1163.
20. Fleming, I. Chemtracts 1991, 4, 21. Also see ref 4b for chelation-controlled open transition structure.
21. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204.
22. (b) Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61-70.
23. (a) Roush, W. R.; VanNieuwenhze, M. S. J. Am. Chem. Soc. 1994, 116, 8536-8543.
24. (b) Keck, G. E.; Abbott, D. E. Tetrahedron Lett. 1984, 25, 1883-1887.
25. Keck, G. E.; Savin, K. A.; Cressman, N. E. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889-7896.
26. Marshall, J. A.; Wang X.-j. J. Org. Chem. 1991, 56, 3211-3213.
27. For the preparation of aldehydes 7a-d, see Supporting Information.
28. 4 proved to be less effective in these crotylation reactions.