Enantioselective Darzens reaction using organoselenide–lithium hydroxide complexes

S Watanabe, R Hasebe, J Ouchi, H Nagasawa…

Index: Watanabe, Shin-Ichi; Hasebe, Risa; Ouchi, Jun; Nagasawa, Hideko; Kataoka, Tadashi Tetrahedron Letters, 2010 , vol. 51, # 44 p. 5778 - 5780

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Citation Number: 9

Abstract

Asymmetric Darzens reaction catalyzed by chiral selenides is described. A novel Lewis acid/Brønsted base catalyst formed by C2 symmetric chiral selenide-bearing isoborneol skeletons, which were readily prepared from (1S)-10-camphorsulfonic acid, and LiOH promoted the reaction of phenacyl bromide with aldehydes to afford the desired trans oxiranes with up to 62% ee.

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