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alpha-Hydroxy Acids in Enantioselective Syntheses

alpha-Hydroxy Acids in Enantioselective Syntheses

Gary M. Coppola, Herbert F. Schuster

ISBN: 978-3-527-60085-4 August 2003 320 Pages


Attention synthetic chemist!

Chiral alpha-hydroxy acids available from nature's chiral pool serve as starting materials in a wide variety of enantioselective conversions leading to commercially important products. This monograph, a stimulating source of ideas and an essential reference work for research chemists, focuses on the well-known lactic, mandelic, malic, and tartaric acids.

Well-chosen examples show how chiral centers inherent in these simple compounds can be used to control the introduction of further stereogenic centers. Readers can directly apply new transformations in their own work since reaction conditions are given in handy tables.
1 Lactic Acid
1.1 Reaction at the Ester Site
1.2 Inversion Reactions
1.3 O-Acyl Lactates
1.4 O-Protected Lactic Acid Derivatives
1.5 O-Protected Lactaldehydes
1.6 D-Lactic Acid Derivatives

2 Mandelic Acid

3 Malic Acid
3.1 The Basics
3.2 Site-Selective Reactions of Malic Acid Derivatives
3.3 Reactions at Both Carboxylate Sites
3.4 (R)-Malic Acid
3.5 Citramalic Acid
3.6 Addenda

4 Tartaric Acid
4.1 O-Isopropylidene Tartaric Acid Derivatives
4.2 O-Benzylidene Tartaric Acid Derivatives
4.3 Miscellaneous Diol-Protected Tartaric Acid Derivatives