Volume 28, Issue 50
Preparative Organic Chemistry
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ChemInform Abstract: Chiral Lewis Acid Controlled Synthesis (CLAC Synthesis): Chiral Lewis Acids Influence the Reaction Course in Asymmetric Aldol Reactions for the Synthesis of Enantiomeric Dihydroxythioester Derivatives in the Presence of Chiral Diamines Derived from L-Proline.

S. KOBAYASHI

S. KOBAYASHI

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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M. HORIBE

M. HORIBE

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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First published: 02 August 2010

Abstract

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ChemInform Abstract

The preparation of both enantiomers of 2,3-dihydroxythioester derivatives with perfect selectivities by using similar types of chiral sources derived from L-proline is described. The chiral diamines used differ only in the fusion point of the benzene ring connected to the pyrrolidine moiety. The unique selectivities are ascribed to the conformational difference between the chiral tin(II) Lewis acids of the chiral diamines.

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