Enantiomerically enriched atropisomeric N,N′-diaryl ureas by oxidative kinetic resolution of their 2-sulfanyl derivatives

Jonathan Clayden; Hazel Turner

doi:10.1016/j.tetlet.2009.02.021

Enantiomerically enriched atropisomeric N,N′-diaryl ureas by oxidative kinetic resolution of their 2-sulfanyl derivatives

Jonathan Clayden, Hazel Turner

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

Abstract

Atropisomeric N-methyl-N,N′-diaryl ureas may be obtained in enantiomerically enriched form by oxidative kinetic resolution of their sulfide derivatives. The atropisomeric sulfides may be obtained in up to 97:3 er and display high stability to racemisation (half-lives at 25 °C of up to 500 years). Unlike related fully alkylated ureas, the product sulfoxides exhibit relatively weak thermodynamic conformational selectivity. © 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3216-3219
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.021
Publication status	Published - 1 Jul 2009

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title = "Enantiomerically enriched atropisomeric N,N′-diaryl ureas by oxidative kinetic resolution of their 2-sulfanyl derivatives",

abstract = "Atropisomeric N-methyl-N,N′-diaryl ureas may be obtained in enantiomerically enriched form by oxidative kinetic resolution of their sulfide derivatives. The atropisomeric sulfides may be obtained in up to 97:3 er and display high stability to racemisation (half-lives at 25 °C of up to 500 years). Unlike related fully alkylated ureas, the product sulfoxides exhibit relatively weak thermodynamic conformational selectivity. {\textcopyright} 2009 Elsevier Ltd. All rights reserved.",

author = "Jonathan Clayden and Hazel Turner",

year = "2009",

month = jul,

day = "1",

doi = "10.1016/j.tetlet.2009.02.021",

language = "English",

volume = "50",

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journal = "Tetrahedron Letters",

issn = "1873-3581",

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T1 - Enantiomerically enriched atropisomeric N,N′-diaryl ureas by oxidative kinetic resolution of their 2-sulfanyl derivatives

AU - Clayden, Jonathan

AU - Turner, Hazel

PY - 2009/7/1

Y1 - 2009/7/1

N2 - Atropisomeric N-methyl-N,N′-diaryl ureas may be obtained in enantiomerically enriched form by oxidative kinetic resolution of their sulfide derivatives. The atropisomeric sulfides may be obtained in up to 97:3 er and display high stability to racemisation (half-lives at 25 °C of up to 500 years). Unlike related fully alkylated ureas, the product sulfoxides exhibit relatively weak thermodynamic conformational selectivity. © 2009 Elsevier Ltd. All rights reserved.

AB - Atropisomeric N-methyl-N,N′-diaryl ureas may be obtained in enantiomerically enriched form by oxidative kinetic resolution of their sulfide derivatives. The atropisomeric sulfides may be obtained in up to 97:3 er and display high stability to racemisation (half-lives at 25 °C of up to 500 years). Unlike related fully alkylated ureas, the product sulfoxides exhibit relatively weak thermodynamic conformational selectivity. © 2009 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2009.02.021

DO - 10.1016/j.tetlet.2009.02.021

M3 - Article

SN - 1873-3581

VL - 50

SP - 3216

EP - 3219

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Enantiomerically enriched atropisomeric N,N′-diaryl ureas by oxidative kinetic resolution of their 2-sulfanyl derivatives

Abstract

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