New Synthesis of (±)-Sitophilate Using Carboxylic Acid Dianion Methodology - A Stereoselectivity Study

Salvador Gil; Margarita Parra; Pablo Rodriguez; Enrique Sotoca

doi:10.1055/s-2005-918466

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New Synthesis of (±)-Sitophilate Using Carboxylic Acid Dianion Methodology - A Stereoselectivity Study

Salvador Gil, Margarita Parra*, Pablo Rodriguez, Enrique Sotoca
Department de Organic Chemistry, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot, Spain
Fax: +34(9)639083152; e-Mail: Margarita.Parra@uv.es;

Abstract

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Abstract

A simple two-step synthesis of (±)-sitophilate in has been developed by addition of propanal to the lithium enediolate of propanoic acid and subsequent esterification with 3-pentanol under standard Fischer conditions. Efforts to control the diastereoselectivity to generate the syn isomer are described. A modest degree of asymmetric induction is found using chiral amides as base.

Key words

carboxylic acids - aldehyde - addition reaction - amino alcohols - diastereoselectivity

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