Enantioselective desymmetrization of meso-cyclic anhydrides catalyzed by hexahydro-1H-pyrrolo[1,2-c] imidazolones

Asymmetric methanolysis of meso cyclic carboxylic anhydrides including hexahydrophthalic anhydride proceeded in toluene in the presence of (6R,7aS)-(2-aryl-6-hydroxy)hexahydro- 1H-pyrrolo[1,2-c]imidazol-1-one to give the corresponding desymmetrized mono ester acids (e.g. (1S,2R)-2- (methoxycarbonyl)...

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Bibliographic Details
Published inTetrahedron letters Vol. 42; no. 3; pp. 411 - 414
Main Authors Uozumi, Y, Yasoshima, K, Miyachi, T, Nagai, S
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 15.01.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
nucleophilic catalyst
ISOPROPYL HEMIESTERS
SECONDARY ALCOHOLS
enantioselective desymmetrization
ASYMMETRIC-SYNTHESIS
pyrrolo[1,2-c]imidazolone
HETEROCYCLES
ACYLATION
ESTERIFICATION
DMAP
ACID ANHYDRIDES
NONENZYMATIC KINETIC RESOLUTION
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Summary:Asymmetric methanolysis of meso cyclic carboxylic anhydrides including hexahydrophthalic anhydride proceeded in toluene in the presence of (6R,7aS)-(2-aryl-6-hydroxy)hexahydro- 1H-pyrrolo[1,2-c]imidazol-1-one to give the corresponding desymmetrized mono ester acids (e.g. (1S,2R)-2- (methoxycarbonyl)cyclohexane-1-carboxylic acid) with enantiomeric excesses of up to 89%. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)01972-9