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Paper | Regular issue | Vol 57, No. 8, 2002, pp.1487-1493
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9516
Asymmetric Nucleophilic Addition Reactions of Aldehydes with Optically Active Dithioacetals and Their Application to Optically Active α-Hydroxy Ketone Synthesis

Hideo Taka, Ken-ichi Fujita,* Akihiro Oishi, and Yoichi Taguchi

*National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan

Abstract

Optically active dithioacetals were prepared by the reaction of acetals with dithiol (1) having a chiral binaphthyl skeleton. Asymmetric addition reactions of various aldehydes with lithiated dithioacetals smoothly proceeded to provide the corresponding chiral alcohols (4) and (5) in fair diastereomeric excess. Moreover, preparation of optically pure α-hydroxy ketone by removal of the chiral auxiliary of 4a was achieved without racemization.