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A Non-Racemic Equivalent of Glycolic Acid: Preparation of both enantiomers from D-mannitol

✍ Scribed by Philippe Renaud; Sokol Abazi

Publisher
John Wiley and Sons
Year
1996
Tongue
German
Weight
327 KB
Volume
79
Category
Article
ISSN
0018-019X

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✦ Synopsis

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A practical synthesis of both enantiomers of 2-(tert-butyl)-Z-methyl-1,3-dioxolan-4-one starting from D-mannitol IS reported These compounds are chiral equivalents of glycolic acid ( = hydroxyacetic acid) which are configurationally stable and can be alkylated via their enolates.

Introduction.

-Recently, we became interested in producing glycolic-acid radicals and applying thein for the synthesis of alkylated CI -hydroxy-or CI -alkoxy-acid derivatives [ 11.

Our final goal is the synthesis of enantiomerically pure cyclic a-hydroxy acids by enolate alkylations and radical cyclizations. For this purpose, we need an easily available nonracemic equivalent of glycolic acid (= hydroxyacetic acid). Several approaches to this problem have been reported in the literature. They are mainly based on acyclic derivatives bearing a chiral ester/amide group [2] or cyclic derivatives with chirality at the acetal OMOM 0 Hefmchen (1984) Pearson (1 986) Kelly (1 984) COOMe j . I I I I (yo Seebacb (1 986) , OMOM MOM0 Kabuki (I 985) 0 Me 1 2 Figure. Chiral non-racemic equivalents of glycolic acid used for the prepurarion of x-liydroxy acids by enalate alkylation ' ) 4,

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