Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective, Catalytic, Tandem Michael/Henry Reaction for the Control of Four Stereocenters

Abstract

A choice of three: The tandem Michael/Henry reaction of a nitroalkene and pentane-1,5-dial (generated in situ) proceeded efficiently when diphenylprolinol silyl ether was used as an organocatalyst to afford substituted nitrocyclohexanecarbaldehydes with high diastereo- and enantioselectivity (see scheme; TMS: trimethylsilyl). Isomerization under basic or acidic conditions diastereoselectively converts the product into two stereoisomers, without compromising the enantioselectivity. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z700909_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.