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Beilstein J Org Chem. 2011;7:1570-6. doi: 10.3762/bjoc.7.185. Epub 2011 Nov 25.

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

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1
Department of Chemistry, Imperial College London, London, SW7 2AZ, England.

Abstract

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.

KEYWORDS:

aryl amino acids; arynes; asymmetric; multicomponent; quaternary

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