Selective β-oxidation of α-sulfanyl amides

Marie Kissane; Maureen Murphy; Lorraine M. Bateman; Daniel G. McCarthy; Anita R. Maguire

doi:10.1016/j.tet.2011.05.041

Selective β-oxidation of α-sulfanyl amides

Marie Kissane
, Maureen Murphy
, Lorraine M. Bateman
, Daniel G. McCarthy
, Anita R. Maguire

University College Cork

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

Abstract

A selective β-oxidation of a series of α-sulfanyl amides to the corresponding β-oxo-α-sulfanyl amides is described. This selective efficient oxidation of an unfunctionalised methyl or methylene group occurs under mild conditions, involving three sequential transformations conducted without isolation of the intermediates. Critically neither the sulfur nor the reactive α-CH bond is affected in the overall process.

Original language	English
Pages (from-to)	5494-5499
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	30
DOIs	https://doi.org/10.1016/j.tet.2011.05.041
Publication status	Published - 29 Jul 2011

Keywords

Organosulfur chemistry
Oxidation
Stereoselective synthesis

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10.1016/j.tet.2011.05.041

https://hdl.handle.net/10468/591Licence: CC BY-NC-ND

Cite this

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title = "Selective β-oxidation of α-sulfanyl amides",

abstract = "A selective β-oxidation of a series of α-sulfanyl amides to the corresponding β-oxo-α-sulfanyl amides is described. This selective efficient oxidation of an unfunctionalised methyl or methylene group occurs under mild conditions, involving three sequential transformations conducted without isolation of the intermediates. Critically neither the sulfur nor the reactive α-CH bond is affected in the overall process.",

keywords = "Organosulfur chemistry, Oxidation, Stereoselective synthesis",

author = "Marie Kissane and Maureen Murphy and Bateman, \{Lorraine M.\} and McCarthy, \{Daniel G.\} and Maguire, \{Anita R.\}",

year = "2011",

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T1 - Selective β-oxidation of α-sulfanyl amides

AU - Kissane, Marie

AU - Murphy, Maureen

AU - Bateman, Lorraine M.

AU - McCarthy, Daniel G.

AU - Maguire, Anita R.

PY - 2011/7/29

Y1 - 2011/7/29

N2 - A selective β-oxidation of a series of α-sulfanyl amides to the corresponding β-oxo-α-sulfanyl amides is described. This selective efficient oxidation of an unfunctionalised methyl or methylene group occurs under mild conditions, involving three sequential transformations conducted without isolation of the intermediates. Critically neither the sulfur nor the reactive α-CH bond is affected in the overall process.

AB - A selective β-oxidation of a series of α-sulfanyl amides to the corresponding β-oxo-α-sulfanyl amides is described. This selective efficient oxidation of an unfunctionalised methyl or methylene group occurs under mild conditions, involving three sequential transformations conducted without isolation of the intermediates. Critically neither the sulfur nor the reactive α-CH bond is affected in the overall process.

KW - Organosulfur chemistry

KW - Oxidation

KW - Stereoselective synthesis

UR - https://www.scopus.com/pages/publications/79959333506

U2 - 10.1016/j.tet.2011.05.041

DO - 10.1016/j.tet.2011.05.041

M3 - Article

AN - SCOPUS:79959333506

SN - 0040-4020

VL - 67

SP - 5494

EP - 5499

JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -

Selective β-oxidation of α-sulfanyl amides

Abstract

Keywords

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