Advances in Organic Synthesis

Volume: 4

Asymmetric Synthesis of α-Unsubstituted β-Hydroxy Acids

Author(s): Jan Spengler and Fernando Albericio

Pp: 3-35 (33)

DOI: 10.2174/9781608054756113040003

* (Excluding Mailing and Handling)


α-Unsubstituted β-hydroxy acids (3-hydroxycarboxylic acids) are constituents of various natural products with pharmacological and other technical properties of interest. They are also important intermediates in organic synthesis. This article reviews various possible routes for asymmetric synthesis of enantiopure or enantiomerically enriched α-unsubstituted β-hydroxy acids.

Keywords: 3-hydroxycarboxylic acids, asymmetric aldol reactions, acetate aldol reactions, Reformatsky reaction, asymmetric reduction, Arndt-Eistert homologation, Wolff-rearrangement, beta-lactones, cyclic sulfites, reductive cleavage, green plastics, statines, 3-hydroxytetradecanoic acid, Mukaiyama aldol reaction, chiral auxiliaries, chiral catalysts, 3-oxo-carboxylic acids, BINAP, asymmetric conjugate radical addition, catalytic desymmetrization.

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