Kinetic resolution of chiral racemic (1R*,3aS*,7aS*)-hexahydro-2-oxobenzofuran-3-ylacetic acid ethyl ester was achieved by means of immobilized Lipozyme(R). At low conversion values, the (-)-acid was isolated with 84% ee, while at high conversion values the (+)-ester was obtained with 98% ee. Their configurations were determined by transformation of the acid into the corresponding alpha-methylene derivative of known absolute configuration.
SYNTHESIS AND BIOLOGICAL RESOLUTION OF CONDENSED BICYCLIC ISOPARACONIC ACID DERIVATIVES / Valentin, Ennio; Drioli, Sara; Felluga, Fulvia; Forzato, Cristina; Pitacco, Giuliana. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1. - ISSN 1364-5463. - STAMPA. - (2000), pp. 2839-2842. [10.1039/b001615m]
SYNTHESIS AND BIOLOGICAL RESOLUTION OF CONDENSED BICYCLIC ISOPARACONIC ACID DERIVATIVES
VALENTIN, ENNIO;DRIOLI, Sara;FELLUGA, FULVIA;FORZATO, Cristina;PITACCO, GIULIANA
2000-01-01
Abstract
Kinetic resolution of chiral racemic (1R*,3aS*,7aS*)-hexahydro-2-oxobenzofuran-3-ylacetic acid ethyl ester was achieved by means of immobilized Lipozyme(R). At low conversion values, the (-)-acid was isolated with 84% ee, while at high conversion values the (+)-ester was obtained with 98% ee. Their configurations were determined by transformation of the acid into the corresponding alpha-methylene derivative of known absolute configuration.Pubblicazioni consigliate
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