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Aluminum chloride‐mediated kinetic resolution of racemic γ‐substituted‐γ‐lactones
Author(s) -
Patil Sudhir T.,
Karnik Anil V.
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20036
Subject(s) - chemistry , kinetic resolution , anhydrous , amide , lactone , chloride , stereochemistry , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis
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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