Volume 27, Issue 11
Preparative Organic Chemistry
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ChemInform Abstract: The Use of Chiral Sulfides in Catalytic Asymmetric Epoxidation.

V. K. AGGARWAL

V. K. AGGARWAL

Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK

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A. THOMPSON

A. THOMPSON

Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK

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R. V. H. JONES

R. V. H. JONES

Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK

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M. STANDEN

M. STANDEN

Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK

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First published: March 12, 1996

Abstract

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ChemInform Abstract

In the presence of the chiral sulfide (V), generated from (+)-10- camphorsulfonyl chloride, phenyl diazomethane reacts with aromatic as well as aliphatic aldehydes yielding oxiranes like (VIII) in good yield with reasonable enantioselectivity. Using its epimer resulting from the thiol (III) lower stereoselectivity is observed.

chemical structure image

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