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

✍ Scribed by Yasuhiro Uozumi; Kayo Yasoshima; Takamasa Miyachi; Shin-ichi Nagai

Book ID: 104211516
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 86 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01972-9

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✦ Synopsis

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%.

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