Diastereoselective oxidation of substituted 1,2-dithiolan-3-ones

Richard S. Glass; Yunqi Liu

doi:10.1016/S0040-4039(00)76693-7

Diastereoselective oxidation of substituted 1,2-dithiolan-3-ones

Richard S. Glass, Yunqi Liu

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

Oxidation of 1,2-dithiolan-3-ones 1 with one equivalent of dimethyldioxirane in dichloromethane at -78°C produces the corresponding 1,2-dithiolan-3-one 1-oxides 2 in high yield and with diastereoselectivities as high as 18:1. The major diastereomer formed is the trans isomer. An X-ray crystallographic structure study of the major diastereomer 2c obtained by oxidation of 1g is reported.

Original language	English (US)
Pages (from-to)	3887-3888
Number of pages	2
Journal	Tetrahedron Letters
Volume	35
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4039(00)76693-7
State	Published - Jun 6 1994

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Diastereoselective oxidation of substituted 1,2-dithiolan-3-ones",

abstract = "Oxidation of 1,2-dithiolan-3-ones 1 with one equivalent of dimethyldioxirane in dichloromethane at -78°C produces the corresponding 1,2-dithiolan-3-one 1-oxides 2 in high yield and with diastereoselectivities as high as 18:1. The major diastereomer formed is the trans isomer. An X-ray crystallographic structure study of the major diastereomer 2c obtained by oxidation of 1g is reported.",

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T1 - Diastereoselective oxidation of substituted 1,2-dithiolan-3-ones

AU - Glass, Richard S.

AU - Liu, Yunqi

PY - 1994/6/6

Y1 - 1994/6/6

N2 - Oxidation of 1,2-dithiolan-3-ones 1 with one equivalent of dimethyldioxirane in dichloromethane at -78°C produces the corresponding 1,2-dithiolan-3-one 1-oxides 2 in high yield and with diastereoselectivities as high as 18:1. The major diastereomer formed is the trans isomer. An X-ray crystallographic structure study of the major diastereomer 2c obtained by oxidation of 1g is reported.

AB - Oxidation of 1,2-dithiolan-3-ones 1 with one equivalent of dimethyldioxirane in dichloromethane at -78°C produces the corresponding 1,2-dithiolan-3-one 1-oxides 2 in high yield and with diastereoselectivities as high as 18:1. The major diastereomer formed is the trans isomer. An X-ray crystallographic structure study of the major diastereomer 2c obtained by oxidation of 1g is reported.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Diastereoselective oxidation of substituted 1,2-dithiolan-3-ones

Abstract

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