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

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

33 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3216-3219
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	26
Early online date	8 Feb 2009
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.",

author = "Jonathan Clayden and Hazel Turner",

year = "2009",

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

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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

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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.

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.

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U2 - 10.1016/j.tetlet.2009.02.021

DO - 10.1016/j.tetlet.2009.02.021

M3 - Article (Academic Journal)

AN - SCOPUS:65549126868

SN - 0040-4039

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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