Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of...

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Main Authors:	Elizabeth P. Jones, Peter Jones, Andrew J. P. White, Anthony G. M. Barrett
Format:	Article
Language:	English
Published:	Beilstein-Institut 2011-11-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	aryl amino acids arynes asymmetric multicomponent quaternary
Online Access:	https://doi.org/10.3762/bjoc.7.185

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spelling	doaj-0dd1b49774a04a25967a1aed4e7448432021-02-02T01:38:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-11-01711570157610.3762/bjoc.7.1851860-5397-7-185Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reactionElizabeth P. Jones0Peter Jones1Andrew J. P. White2Anthony G. M. Barrett3Department of Chemistry, Imperial College London, London, SW7 2AZ, EnglandWorldwide Medicinal Chemistry, Pfizer Limited, Ramsgate Road, Sandwich, Kent, CT13 9NJ, EnglandDepartment of Chemistry, Imperial College London, London, SW7 2AZ, EnglandDepartment of Chemistry, Imperial College London, London, SW7 2AZ, EnglandA method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.https://doi.org/10.3762/bjoc.7.185aryl amino acidsarynesasymmetricmulticomponentquaternary
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Elizabeth P. Jones Peter Jones Andrew J. P. White Anthony G. M. Barrett
spellingShingle	Elizabeth P. Jones Peter Jones Andrew J. P. White Anthony G. M. Barrett Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction Beilstein Journal of Organic Chemistry aryl amino acids arynes asymmetric multicomponent quaternary
author_facet	Elizabeth P. Jones Peter Jones Andrew J. P. White Anthony G. M. Barrett
author_sort	Elizabeth P. Jones
title	Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction
title_short	Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction
title_full	Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction
title_fullStr	Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction
title_full_unstemmed	Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction
title_sort	asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2011-11-01
description	A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.
topic	aryl amino acids arynes asymmetric multicomponent quaternary
url	https://doi.org/10.3762/bjoc.7.185
work_keys_str_mv	AT elizabethpjones asymmetricsynthesisofquaternaryarylaminoacidderivativesviaathreecomponentarynecouplingreaction AT peterjones asymmetricsynthesisofquaternaryarylaminoacidderivativesviaathreecomponentarynecouplingreaction AT andrewjpwhite asymmetricsynthesisofquaternaryarylaminoacidderivativesviaathreecomponentarynecouplingreaction AT anthonygmbarrett asymmetricsynthesisofquaternaryarylaminoacidderivativesviaathreecomponentarynecouplingreaction
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Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

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