Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides

Marie Kissane; Simon E. Lawrence; Anita R. Maguire

doi:10.1016/j.tetasy.2010.05.004

Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides

University College Cork

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

Abstract

Diastereoselective sulfur oxidation in 2-thio-3-chloroacrylamides is described. A range of chiral amine auxiliaries was incorporated in the β-chloroacrylamide, and the efficiency with which the stereochemistry was relayed to the sulfur centre during sulfoxidation was investigated. Diastereomeric ratios of up to 3.3:1 were achieved.

Original language	English
Pages (from-to)	871-884
Number of pages	14
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	7
DOIs	https://doi.org/10.1016/j.tetasy.2010.05.004
Publication status	Published - 21 Apr 2010

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10.1016/j.tetasy.2010.05.004

https://hdl.handle.net/10468/587Licence: CC BY-NC-ND

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title = "Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides",

abstract = "Diastereoselective sulfur oxidation in 2-thio-3-chloroacrylamides is described. A range of chiral amine auxiliaries was incorporated in the β-chloroacrylamide, and the efficiency with which the stereochemistry was relayed to the sulfur centre during sulfoxidation was investigated. Diastereomeric ratios of up to 3.3:1 were achieved.",

author = "Marie Kissane and Lawrence, \{Simon E.\} and Maguire, \{Anita R.\}",

year = "2010",

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day = "21",

doi = "10.1016/j.tetasy.2010.05.004",

language = "English",

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T1 - Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides

AU - Kissane, Marie

AU - Lawrence, Simon E.

AU - Maguire, Anita R.

PY - 2010/4/21

Y1 - 2010/4/21

N2 - Diastereoselective sulfur oxidation in 2-thio-3-chloroacrylamides is described. A range of chiral amine auxiliaries was incorporated in the β-chloroacrylamide, and the efficiency with which the stereochemistry was relayed to the sulfur centre during sulfoxidation was investigated. Diastereomeric ratios of up to 3.3:1 were achieved.

AB - Diastereoselective sulfur oxidation in 2-thio-3-chloroacrylamides is described. A range of chiral amine auxiliaries was incorporated in the β-chloroacrylamide, and the efficiency with which the stereochemistry was relayed to the sulfur centre during sulfoxidation was investigated. Diastereomeric ratios of up to 3.3:1 were achieved.

UR - https://www.scopus.com/pages/publications/77956460095

U2 - 10.1016/j.tetasy.2010.05.004

DO - 10.1016/j.tetasy.2010.05.004

M3 - Article

AN - SCOPUS:77956460095

SN - 0957-4166

VL - 21

SP - 871

EP - 884

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 7

ER -

Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides

Abstract

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