Diastereoselective oxidation of substituted thietanes and stereoselective oxidation of their sulfoxides

Richard S. Glass; Waheguru Pal Singh; Bruce A. Hay

doi:10.1016/S0040-4039(00)78190-1

Diastereoselective oxidation of substituted thietanes and stereoselective oxidation of their sulfoxides

Richard S. Glass, Waheguru Pal Singh, Bruce A. Hay

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

5 Scopus citations

Abstract

Oxidation of substituted thietanes 1a, b, and 6 with m-chloroperoxybenzoic acid preferentially gives the corresponding cis-sulfoxides with modest diastereoselectivity. Selective oxidation of the trans over the cis diastereomeric pairs of sulfoxides 2a, 3a; 2b, 3b; 7, 8 occurs with moderate selectivity with m-chloroperoxybenzoic acid. The basis for these selectivities is hydrogen bonding between the 3-substituent and the peracid.

Original language	English (US)
Pages (from-to)	5809-5812
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(00)78190-1
State	Published - Aug 8 1994
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Diastereoselective oxidation of substituted thietanes and stereoselective oxidation of their sulfoxides",

abstract = "Oxidation of substituted thietanes 1a, b, and 6 with m-chloroperoxybenzoic acid preferentially gives the corresponding cis-sulfoxides with modest diastereoselectivity. Selective oxidation of the trans over the cis diastereomeric pairs of sulfoxides 2a, 3a; 2b, 3b; 7, 8 occurs with moderate selectivity with m-chloroperoxybenzoic acid. The basis for these selectivities is hydrogen bonding between the 3-substituent and the peracid.",

author = "Glass, {Richard S.} and {Pal Singh}, Waheguru and Hay, {Bruce A.}",

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T1 - Diastereoselective oxidation of substituted thietanes and stereoselective oxidation of their sulfoxides

AU - Glass, Richard S.

AU - Pal Singh, Waheguru

AU - Hay, Bruce A.

PY - 1994/8/8

Y1 - 1994/8/8

N2 - Oxidation of substituted thietanes 1a, b, and 6 with m-chloroperoxybenzoic acid preferentially gives the corresponding cis-sulfoxides with modest diastereoselectivity. Selective oxidation of the trans over the cis diastereomeric pairs of sulfoxides 2a, 3a; 2b, 3b; 7, 8 occurs with moderate selectivity with m-chloroperoxybenzoic acid. The basis for these selectivities is hydrogen bonding between the 3-substituent and the peracid.

AB - Oxidation of substituted thietanes 1a, b, and 6 with m-chloroperoxybenzoic acid preferentially gives the corresponding cis-sulfoxides with modest diastereoselectivity. Selective oxidation of the trans over the cis diastereomeric pairs of sulfoxides 2a, 3a; 2b, 3b; 7, 8 occurs with moderate selectivity with m-chloroperoxybenzoic acid. The basis for these selectivities is hydrogen bonding between the 3-substituent and the peracid.

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U2 - 10.1016/S0040-4039(00)78190-1

DO - 10.1016/S0040-4039(00)78190-1

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VL - 35

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EP - 5812

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Diastereoselective oxidation of substituted thietanes and stereoselective oxidation of their sulfoxides

Abstract

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