Diastereo-and Enantioselective Synthesis of syn-and anti-1, 2-Diol Units by Asymmetric Aldol Reactions.

T Mukaiyama, I Shiina, H Uchiro…

Index: Mukaiyama, Teruaki; Shiina, Isamu; Uchiro, Hiromi; Kobayashi, Shu Bulletin of the Chemical Society of Japan, 1994 , vol. 67, # 6 p. 1708 - 1716

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Citation Number: 53

Abstract

syn-and anti-1, 2-Diol units were prepared by using asymmetric aldol reactions of the silyl enol ethers derived from α-alkoxythioacetic S-esters with aldehydes. In the presence of tin (II) triflate, a chiral diamine, and dibutyltin diacetate,(Z)-2-benzyloxy-1-ethylthino-1- (trimethylsiloxy) ethene reacted with aldehydes to afford the corresponding anti-aldol adducts in high yields with excellent diastereo-and enantioselectivities, while syn-adducts ...