Enzymatic hydrolysis and esterification. Routes to optically pure cyclopentanols
Authors:
- 1 January 1991
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 110 (5) , 171-174
Abstract
Using an esterhydrolase from Pseudomonas sp. (SAM II), a series of optically pure cyclopentanols 1‐4 was prepared by enzymatic hydrolysis of their corresponding acetates. Using the same enzyme, these cyclopentanols were esterified by enol esters as acyl donors. Due to identical stereochemical recognition in both reaction modes, opposite pairs of enantiomeres were obtained.Keywords
This publication has 27 references indexed in Scilit:
- Enzymic preparation of tetrahydrofuran derivatives of high optical purityJournal of the Chemical Society, Perkin Transactions 1, 1990
- Enzyme-catalyzed asymmetric synthesis. 8. Enantioselectivity of pig liver esterase catalyzed hydrolyses of 4-substituted meso cyclopentane 1,2-diestersThe Journal of Organic Chemistry, 1989
- Enantiomerically pure cyclohexanols and cyclohexane-1,2-diol derivatives; chiral auxiliaries and substitutes for (–)-8-phenylmenthol. A facile enzymatic routeJournal of the Chemical Society, Chemical Communications, 1989
- An efficient synthesis of both enantiomers of trans-1,2-cyclopentanediol and their conversion to two novel bidentate phosphite and fluorophosphinite ligandsThe Journal of Organic Chemistry, 1988
- Synthesis of (1S,4R)-(-)-4-Hydroxy-2-cyclopentenyl Acetate by a Highly Enantioselective Enzyme-Catalyzed Transesterification in Organic SolventsSynthesis, 1988
- Enantioselective hydrolysis of five-membered-ring acetates catalysed by Pseudomonas fluorescens lipaseJournal of the Chemical Society, Chemical Communications, 1987
- Asymmetric induction in the cycloaddition reactions of the N-sulphinylcarbamate of 8-phenylmentholJournal of the Chemical Society, Chemical Communications, 1985
- Stereoselektive Synthese enantiomerenreiner Naturstoffe — Beispiel ÖstronAngewandte Chemie, 1983
- Chiral crown ethers derived from (+)-(1S, 2S)-trans-cyclohexane-1,2-diolJournal of the Chemical Society, Perkin Transactions 1, 1976
- Potential Anticancer Agents.1 I. Model Experiments for Synthesis of 2'-Deoxynucleosides by the 2,3-Episulfide ApproachJournal of the American Chemical Society, 1958