Synthesis and stereoselective oxidation of α-thio-β- chloropropenyloxazolidin-2-ones

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

doi:10.1016/j.tetasy.2010.10.007

Synthesis and stereoselective oxidation of α-thio-β- chloropropenyloxazolidin-2-ones

Marie Kissane
, Maureen Murphy
, Simon E. Lawrence
, Anita R. Maguire

University College Cork

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

Abstract

The investigation of the stereoselective reaction of α- thiopropanoyloxazolidin-2-ones with NCS to yield α-thio-β- chloropropenyloxazolidin-2-ones is described. Diastereoselective sulfur oxidation of the resulting α-thio-β-chloropropenyloxazolidin-2-ones shows modest diastereocontrol. However, via a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation, diastereoselectivities of up to 94% de have been achieved.

Original language	English
Pages (from-to)	2550-2558
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	20
DOIs	https://doi.org/10.1016/j.tetasy.2010.10.007
Publication status	Published - 28 Oct 2010

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https://hdl.handle.net/10468/577Licence: CC BY-NC-ND

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title = "Synthesis and stereoselective oxidation of α-thio-β- chloropropenyloxazolidin-2-ones",

abstract = "The investigation of the stereoselective reaction of α- thiopropanoyloxazolidin-2-ones with NCS to yield α-thio-β- chloropropenyloxazolidin-2-ones is described. Diastereoselective sulfur oxidation of the resulting α-thio-β-chloropropenyloxazolidin-2-ones shows modest diastereocontrol. However, via a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation, diastereoselectivities of up to 94\% de have been achieved.",

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

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T1 - Synthesis and stereoselective oxidation of α-thio-β- chloropropenyloxazolidin-2-ones

AU - Kissane, Marie

AU - Murphy, Maureen

AU - Lawrence, Simon E.

AU - Maguire, Anita R.

PY - 2010/10/28

Y1 - 2010/10/28

N2 - The investigation of the stereoselective reaction of α- thiopropanoyloxazolidin-2-ones with NCS to yield α-thio-β- chloropropenyloxazolidin-2-ones is described. Diastereoselective sulfur oxidation of the resulting α-thio-β-chloropropenyloxazolidin-2-ones shows modest diastereocontrol. However, via a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation, diastereoselectivities of up to 94% de have been achieved.

AB - The investigation of the stereoselective reaction of α- thiopropanoyloxazolidin-2-ones with NCS to yield α-thio-β- chloropropenyloxazolidin-2-ones is described. Diastereoselective sulfur oxidation of the resulting α-thio-β-chloropropenyloxazolidin-2-ones shows modest diastereocontrol. However, via a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation, diastereoselectivities of up to 94% de have been achieved.

UR - https://www.scopus.com/pages/publications/78649330862

U2 - 10.1016/j.tetasy.2010.10.007

DO - 10.1016/j.tetasy.2010.10.007

M3 - Article

AN - SCOPUS:78649330862

SN - 0957-4166

VL - 21

SP - 2550

EP - 2558

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 20

ER -

Synthesis and stereoselective oxidation of α-thio-β- chloropropenyloxazolidin-2-ones

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