Intramolecular arylation of amino acid enolates

Rachel C. Atkinson; Daniel J. Leonard; Julien Maury; Daniele Castagnolo; Nicole Volz; Jonathan Clayden

doi:10.1039/c3cc46193a

Intramolecular arylation of amino acid enolates

Rachel C. Atkinson, Daniel J. Leonard, Julien Maury, Daniele Castagnolo, Nicole Volz, Jonathan Clayden

The University of Manchester

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Abstract

Dianionic enolates formed from N′-aryl urea derivatives of amino acids undergo intramolecular C-arylation by attack of the enolate anion on the N′-aryl ring, leading to a hydantoin derivative of a quaternary amino acid. In situ IR studies allow identification of four intermediates on the reaction pathway. © 2013 The Royal Society of Chemistry.

Original language	English
Pages (from-to)	9734-9736
Number of pages	2
Journal	Chemical Communications
Volume	49
Issue number	84
DOIs	https://doi.org/10.1039/c3cc46193a
Publication status	Published - 28 Oct 2013

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title = "Intramolecular arylation of amino acid enolates",

abstract = "Dianionic enolates formed from N′-aryl urea derivatives of amino acids undergo intramolecular C-arylation by attack of the enolate anion on the N′-aryl ring, leading to a hydantoin derivative of a quaternary amino acid. In situ IR studies allow identification of four intermediates on the reaction pathway. {\textcopyright} 2013 The Royal Society of Chemistry.",

author = "Atkinson, {Rachel C.} and Leonard, {Daniel J.} and Julien Maury and Daniele Castagnolo and Nicole Volz and Jonathan Clayden",

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T1 - Intramolecular arylation of amino acid enolates

AU - Atkinson, Rachel C.

AU - Leonard, Daniel J.

AU - Maury, Julien

AU - Castagnolo, Daniele

AU - Volz, Nicole

AU - Clayden, Jonathan

PY - 2013/10/28

Y1 - 2013/10/28

N2 - Dianionic enolates formed from N′-aryl urea derivatives of amino acids undergo intramolecular C-arylation by attack of the enolate anion on the N′-aryl ring, leading to a hydantoin derivative of a quaternary amino acid. In situ IR studies allow identification of four intermediates on the reaction pathway. © 2013 The Royal Society of Chemistry.

AB - Dianionic enolates formed from N′-aryl urea derivatives of amino acids undergo intramolecular C-arylation by attack of the enolate anion on the N′-aryl ring, leading to a hydantoin derivative of a quaternary amino acid. In situ IR studies allow identification of four intermediates on the reaction pathway. © 2013 The Royal Society of Chemistry.

U2 - 10.1039/c3cc46193a

DO - 10.1039/c3cc46193a

M3 - Article

C2 - 24022183

SN - 1359-7345

VL - 49

SP - 9734

EP - 9736

JO - Chemical Communications

JF - Chemical Communications

IS - 84

ER -

Intramolecular arylation of amino acid enolates

Abstract

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