Enantioselective synthesis of b-Amino acids. 12. experimental and theoretical study of the diastereoselectivity of alkylation of the dianion of N',N'-Bis(a-phenylethyl)-N -carbobenzyloxypropionamide

Enantioselective synthesis of b-Amino acids. 12. experimental and theoretical study of the diastereoselectivity of alkylation of the dianion of N',N'-Bis(a-phenylethyl)-N -carbobenzyloxypropionamide

Achiral, inexpensive beta-alanine was converted into the title chiral amide 1 in 53% overall yield. C-Alkylation of (R,R)-1 required formation of its dianion derivative, (R,R)-1-Li2, which was best achieved by direct metallation with two equivalents of n-BuLi in THF solution and at -78°C. Treatment...

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Bibliographic Details
Main Authors: Gutiérrez-García Víctor Manuel, Reyes-Rangel Gloria, Muñoz-Muñiz Omar, Juaristi Eusebio
Format: Article
Language:English
Published: Sociedade Brasileira de Química 2001-01-01
Series:Journal of the Brazilian Chemical Society
Subjects:
Amino acids
diastereoselective alkylation
enolates
theoretical studies
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000500008

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http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000500008

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