Diphenylprolinol Silyl Ether as a Catalyst in an Asymmetric, Catalytic, and Direct Michael Reaction of Nitroethanol with alpha,beta-Unsaturated Aldehydes

作者：Gotoh Hiroaki; Okamura Daichi; Ishikawa Hayato; Hayashi Yujiro^*

来源：Organic Letters, 2009, 11(18): 4056-4059.

DOI：10.1021/ol901483x

Diphenylprolinol silyl ether was found to be an effective organocatalyst in the enantioselective and direct Michael reaction of nitroethanol and alpha,beta-unsaturated aldehydes, affording the 1-hydroxy-trans-3,4-disubstituted tetrahydropyrans after isomerization. The generated Michael addition products are useful synthetic Intermediates, which can be converted Into chiral tetrahydropyran with a quaternary stereocenter, 3-substituted cis- and trans-prolines, and alpha-amino acid derivatives.

• 出版日期2009-9-17