Highly Stereoselective TiCl₄-Mediated Aldol Reactions from (S)-2-Benzyloxy-3-pentanone

Victor Rodríguez-Cisterna, Cristina Villar, Pedro Romea* and Fèlix Urpí*

*Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain, Email: felix.urpiub.edu, pedro.romeaub.edu

V. Rodríquez-Cisterna, C. Villar, P. Romea, F. Urpi, J. Org. Chem., 2007, 72, 6631-6633.

DOI: 10.1021/jo071048z

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Abstract

The stereoselectivity of TiCl₄-mediated aldol reactions from (S)-2-benzyloxy-3-pentanone is dramatically improved when the reaction is carried out in the presence of 1.1 equiv of tetrahydrofuran or 1,2-dimethoxyethane. 2,4-syn-4,5-syn adducts are then obtained in diastereomeric ratios up to 97:3.

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Key Words

Aldol Addition

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ID: J42-Y2007-2750