Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by chiral N,N′-dioxides and monodentate N-oxides

Tetrahedron Letters

Volumn 45, Issue 1, 2004, Pages 61-64

  Nakajima, Makoto ^a   Yokota, Takaaki ^a   Saito, Makoto ^a   Hashimoto, Shunichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Aldol reaction; Catalyst; Diastereoselectivity; Enantioselectivity; N oxide; Trichlorosilyl enol ether

Indexed keywords

CARBON; ETHER DERIVATIVE; OXIDE;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DONOR; ENANTIOSELECTIVITY; STEREOISOMERISM;

EID: 0742304468     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.114     Document Type: Article

References (33)

1. Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389.
2. Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141.
3. Mahrwald R. Chem. Rev. 99:1999;1095-1120.
4. Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. Engl. 39:2000;1352-1374.
5. Carreira E.M. Jacobsen E.M., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. III:1999;997-1065 Springer, Berlin.
6. Sodeoka M., Ohrai K., Shibasaki M. J. Org. Chem. 60:1995;2648-2649.
7. Kuwano R., Miyazaki H., Ito Y. Chem. Commun. 1998;71-72.
8. Other recent examples of enantioselective aldol reactions: Ito Y., Sawamura M., Hayashi T. J. Am. Chem. Soc. 108:1986;6405-6406.
9. Sasai H., Suzuki T., Arai S., Arai T., Shibasaki M. J. Am. Chem. Soc. 114:1992;4418-4420.
10. Yanagisawa A., Matsumoto Y., Nakashima H., Asakawa K., Yamamoto Y. J. Am. Chem. Soc. 119:1997;9319-9320.
11. Yamada Y.M.A., Yoshikawa N., Sasai H., Shibasaki M. Angew. Chem., Int. Ed. Engl. 36:1997;1871-1873.
12. List B., Lerner R.A., Barbas C.F. J. Am. Chem. Soc. 122:2000;2395-2396.
13. Trost B.M., Ito H. J. Am. Chem. Soc. 122:2000;12003-12004.
14. Northrup A.B., MacMillan D.W.C. J. Am. Chem. Soc. 24:2002;6798-6799.
15. Evans D.A., Downey C.W., Hubbs J.L. J. Am. Chem. Soc. 125:2003;8706-8707.
16. Chuit C., Corriu R.J.P., Reye C., Young J.C. Chem. Rev. 93:1993;1371-1448.
17. Denmark S.E., Winter S.B.D., Su X., Wong K.-T. J. Am. Chem. Soc. 118:1996;7404-7405.
18. Denmark S.E., Su X., Nishigaichi Y. J. Am. Chem. Soc. 120:1998;12990-12991.
19. Denmark S.E., Stavenger R.A. Acc. Chem. Res. 33:2000;432-440.
20. Denmark S.E., Ghosh S.K. Angew. Chem., Int. Ed. 40:2001;4759-4762.
21. Denmark S.E., Fan Y. J. Am. Chem. Soc. 124:2002;4233-4235.
22. Nakajima M., Sasaki Y., Shiro M., Hashimoto S. Tetrahedron: Asymmetry. 8:1997;341-344.
23. Nakajima M., Sasaki Y., Iwamoto H., Hashimoto S. Tetrahedron Lett. 39:1998;87-88.
24. Saito M., Nakajima M., Hashimoto S. Chem. Commun. 2000;1851-1852.
25. Nakajima M., Yamaguchi Y., Hashimoto S. Chem. Commun. 2001;1596-1597.
26. Nakajima M., Saito M., Uemura M., Hashimoto S. Tetrahedron Lett. 43:2002;8827-8829.
27. Nakajima M., Saito M., Shiro M., Hashimoto S. J. Am. Chem. Soc. 120:1998;6419-6420.
28. Recently, Denmark has reported the aldol reaction of trichlorosilyl ketene acetal with ketone catalyzed by 1 or 2 , see Ref. [6e].
29. 2, hexane/AcOEt=10/1) to give the corresponding aldol adduct as a diastereomeric mixture.
30. Malkov A.V., Dufková L., Farrugia L., Kocovsky P. Angew. Chem., Int. Ed. 42:2003;3674-3677.
31. w=0.086.
32. A calculation study revealed that the cationic trigonal bipyramid structure prefers the boat form Gung B.W., Zhu Z., Fouch R.A. J. Org. Chem. 60:1995;2860-2864.
33. The aldol reaction of (E)- or (Z)-4 and benzaldehyde did not proceed with the aid of (R)-7 . The reaction of (Z)-5 and benzaldehyde proceeded (-78°C, 7 h, 85%) in the presence of (R)-7 to predominantly afford the syn-adduct (syn/anti=24:1) with low enantioselectivity. For steric reasons, a chair-like six-membered structure might be preferred even in a cationic trigonal bipyramid transition state, although the details are unclear at this time.