Synthesis and biological resolution of condensed bicyclic isoparaconic acid derivatives

Authors
Drioli, S Felluga, F Forzato, C Pitacco, G Valentin, E
Citation
S. Drioli et al., Synthesis and biological resolution of condensed bicyclic isoparaconic acid derivatives, J CHEM S P1, (16), 2000, pp. 2839-2842
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
16
Year of publication
2000
Pages
2839 - 2842
Database
ISI
SICI code
1470-4358(2000):16<2839:SABROC>2.0.ZU;2-1
Abstract
Kinetic resolution of chiral racemic (1R*,3aS*,7aS*)-hexahydro-2-oxobenzofu ran-3-ylacetic acid ethyl ester was achieved by means of immobilized Lipozy me(R). At low conversion values, the (-)-acid was isolated with 84% ee, whi le at high conversion values the (+)-ester was obtained with 98% ee. Their configurations were determined by transformation of the acid into the corre sponding alpha-methylene derivative of known absolute configuration.