Volume 31, Issue 43
Preparative Organic Chemistry
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ChemInform Abstract: Asymmetric Aldol Reactions Using (S,S)-(+)-Pseudoephedrine-Based Amides: Stereoselective Synthesis of α-Methyl-β-hydroxy Acids, Esters, Ketones, and 1,3-syn and 1,3-anti Diols.

Jose L. Vicario

Jose L. Vicario

Dep. Quim. Org., Fac. Cienc., Univ. Pais Vasco, E-48080 Bilbao, Spain

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Dolores Badia

Dolores Badia

Dep. Quim. Org., Fac. Cienc., Univ. Pais Vasco, E-48080 Bilbao, Spain

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Esther Dominguez

Esther Dominguez

Dep. Quim. Org., Fac. Cienc., Univ. Pais Vasco, E-48080 Bilbao, Spain

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Monica Rodriguez

Monica Rodriguez

Dep. Quim. Org., Fac. Cienc., Univ. Pais Vasco, E-48080 Bilbao, Spain

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Luisa Carrillo

Luisa Carrillo

Dep. Quim. Org., Fac. Cienc., Univ. Pais Vasco, E-48080 Bilbao, Spain

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First published: 01 June 2010

Abstract

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ChemInform Abstract

A very efficient method for performing highly stereoselective aldol reactions is developed. The resulting products can easily be transformed into α-methyl-β-hydroxy acids, esters, and ketones as well as 1,3-syn and 1,3-anti diols without racemization. The pheromones ent-sitophilure (VIIId) and ent-sitophilate (VIc) are available using this method.

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