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

Autor: Elizabeth P. Jones, Peter Jones, Andrew J. P. White, Anthony G. M. Barrett
Jazyk: angličtina
Rok vydání: 2011
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 7, Iss 1, Pp 1570-1576 (2011)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.7.185
Popis: 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.
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