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Aluminum chloride-mediated kinetic resolution of racemic γ-substituted-γ-lactones

✍ Scribed by Sudhir T. Patil; Anil V. Karnik

Book ID
102075777
Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
130 KB
Volume
16
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

Preparation of chiral γ‐substituted‐γ‐lactones (1) through kinetic resolution is described. (S)‐(–)‐1‐Phenylethylamine (2) in the presence of anhydrous AlCl~3~ shows satisfactory levels of enantioselection in reaction with racemic γ‐substituted‐γ‐lactones 1, where (R)‐1 remains unreacted, while (S)‐1 is enantioselectively converted to the ring‐opened amide (S,S)‐4. The enantiopurity of (R)‐(+)‐ γ‐substituted γ‐lactones recovered ranges from 62–98% ee. Chirality 16:336–338, 2004. © 2004 Wiley‐Liss, Inc.

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