Lewis base activation of Lewis acids. Vinylogous aldol addition reactions of conjugated N,O-silyl ketene acetals to aldehydes

Journal of the American Chemical Society

Volumn 128, Issue 4, 2006, Pages 1038-1039

  Denmark, Scott E ^a   Heemstra Jr , John R ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ALDEHYDE; KETENE DERIVATIVE; LEWIS ACID; LEWIS BASE; NATURAL PRODUCT; POLYOL;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CONJUGATION; ENANTIOSELECTIVITY; MUKAIYAMA REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ACETALS; ALDEHYDES; ETHYLENES; KETONES; SILANES; VINYL COMPOUNDS;

EID: 31944440611     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056747c     Document Type: Article

References (28)

1. O'Hagan, D. The Polyketide Metabolites, 1st ed.; Ellis Horwood: Chichester, 1991.
2. (a) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004.
3. (b) Carreira, E. M. In Modern Carbonyl Chemistry: Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 8.
4. (c) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag, Heidelberg, 1999; Vol. III, Chapter 29.
5. (d) Paterson, I.; Cowden, C. J.; Wallace, D. J. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 9.
6. (e) Carreira, E. M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 8B2.
7. (a) Fuson, R. C. Chem. Rev. 1935, 16, 1-27.
8. (b) Krishnamurthy, S. J. Chem. Educ. 1982, 59, 543-547.
9. (c) Bruneau, P.; Taylor, P. J.; Wilkinson, A. J. J. Chem. Soc., Perkin Trans. 2 1996, 2263-2269.
10. (a) Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682-4698.
11. (b) Kalesse, M. Top. Curr. Chem. 2005, 244, 43-76.
12. Catalyst (R,R)-3 is commercially available from Obiter Research, LLC. Contact waboulanger@obiterresearch.com.
13. (a) Denmark, S. E.; Beutner, G. L.; Wynn, T.; Eastgate, M. D. J. Am. Chem. Soc. 2005, 127, 3774-3789.
14. (b) Denmark, S. E.; Beutner, G. L. J. Am. Chem. Soc. 2003, 125, 7800-7801.
15. For a recent application of our method in total synthesis, see: (c) Aubele, D. L.; Wan, S.; Floreancig, P. E. Angew. Chem., Int. Ed. 2005, 44, 3485-3488.
16. Denmark, S. E.; Heemstra, J. R., Jr. Synlett 2004, 2411-2416.
17. Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929-1972.
18. Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 112, 9672-1974.
19. O'Neill, B. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford; 1991; Vol. 1, pp 397-458.
20. For an example of diastereoselective additions of vinylketene silyl N,O-acetals to aldehydes, see: Shirokawa, S.; Kamiyama, M.; Nakamura, T.; Okada, M.; Nakazaki, A.; Hosokawa, S.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 13604-13605.
21. The addition of tetrabutylammonium trifluoromethanesulfonate and diisopropylethylamine to the solution was found to increase the yield of the aldol adducts. For a discussion of the role of these additives, see ref 6a.
22. 4). Nunez, M. T.; Martin, V. S. J. Org. Chem. 1990, 55, 1928-1932.
23. (a) N,O-Silyl ketene acetal 22 is formed as a 2.6:1, E/Z mixture, whereas 23 is a 19:1 Z/E mixture,
24. (b) Product 24 formed as a single E isomer whereas 25 is formed as an 88:12, E/Z mixture.
25. Ketene acetals 22 and 23 also reacted with excellent yield and enantioselectivity with benzaldehyde (90-97% yield, 98.4:1.6-98.6:1.4 er) and cinnamaldehyde (95-97% yield, 98.9:1.1-99.3:0.7 er).
26. (a) Martin, R.; Romea, P.; Tey, C.; Urpi, F.; Vilarrasa, J. Synlett 1997, 1414-1416.
27. (b) Tosaki, S.; Horiuchi, Y.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Chem.-Eur. J. 2004, 10, 1527-1544.
28. Harrington, P. E.; Tius, M. A. Org. Lett. 2000, 2, 2447-2450.