A highly diastereoselective chloride-mediated dynamic kinetic resolution at phosphorus on-route to a key intermediate in the synthesis of GSK2248761A

Alan Ironmonger; Mark Shipton; Fiona Slater; Pete Szeto; Matthew Unthank; Francois-Rene Alexandre; Catherine Caillet; Cyril Dousson

doi:10.1016/j.tetlet.2018.04.018

A highly diastereoselective chloride-mediated dynamic kinetic resolution at phosphorus on-route to a key intermediate in the synthesis of GSK2248761A

Alan Ironmonger, Mark Shipton, Fiona Slater, Pete Szeto, Matthew Unthank, Francois-Rene Alexandre, Catherine Caillet, Cyril Dousson

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Abstract

A highly diastereoselective chloride-mediated dynamic kinetic resolution at phosphorus has been developed to access a key intermediate in the synthesis of GSK2248761A. This procedure utilises a soluble chloride source and a cheap readily available chiral auxiliary. The practicality of this transformation is demonstrated on a multi-gram scale.

Original language	English
Pages (from-to)	2154-2156
Number of pages	3
Journal	Tetrahedron Letters
Volume	59
Issue number	22
Early online date	11 Apr 2018
DOIs	https://doi.org/10.1016/j.tetlet.2018.04.018
Publication status	Published - 30 May 2018

Keywords

Asymmetric synthesis
Chiral phosphorus
Dynamic kinetic resolution
GSK2248761A
Phenylglycine methyl ester

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10.1016/j.tetlet.2018.04.018

Proof_pagination_TETL_49881Accepted author manuscript, 765 KB

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AU - Ironmonger, Alan

AU - Shipton, Mark

AU - Slater, Fiona

AU - Szeto, Pete

AU - Unthank, Matthew

AU - Alexandre, Francois-Rene

AU - Caillet, Catherine

AU - Dousson, Cyril

PY - 2018/5/30

Y1 - 2018/5/30

N2 - A highly diastereoselective chloride-mediated dynamic kinetic resolution at phosphorus has been developed to access a key intermediate in the synthesis of GSK2248761A. This procedure utilises a soluble chloride source and a cheap readily available chiral auxiliary. The practicality of this transformation is demonstrated on a multi-gram scale.

AB - A highly diastereoselective chloride-mediated dynamic kinetic resolution at phosphorus has been developed to access a key intermediate in the synthesis of GSK2248761A. This procedure utilises a soluble chloride source and a cheap readily available chiral auxiliary. The practicality of this transformation is demonstrated on a multi-gram scale.

KW - Asymmetric synthesis

KW - Chiral phosphorus

KW - Dynamic kinetic resolution

KW - GSK2248761A

KW - Phenylglycine methyl ester

UR - https://www.scopus.com/pages/publications/85046142389

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DO - 10.1016/j.tetlet.2018.04.018

M3 - Article

SN - 0040-4039

VL - 59

SP - 2154

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 22

ER -

A highly diastereoselective chloride-mediated dynamic kinetic resolution at phosphorus on-route to a key intermediate in the synthesis of GSK2248761A

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Keywords

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