AN IMPROVED PROCEDURE FOR THE LIPASE-CATALYZED KINETIC RESOLUTION OF ENDO-ENDO-CIS-BICYCLO[3.3.0]OCTANE-2,6-DIOL - SYNTHESIS OF POTENTIAL C-2-SYMMETRICAL ENANTIOMERICALLY PURE BIDENTATE AUXILIARIES

Authors
LEMKE K BALLSCHUH S KUNATH A THEIL F
Citation
K. Lemke et al., AN IMPROVED PROCEDURE FOR THE LIPASE-CATALYZED KINETIC RESOLUTION OF ENDO-ENDO-CIS-BICYCLO[3.3.0]OCTANE-2,6-DIOL - SYNTHESIS OF POTENTIAL C-2-SYMMETRICAL ENANTIOMERICALLY PURE BIDENTATE AUXILIARIES, Tetrahedron : asymmetry, 8(12), 1997, pp. 2051-2055
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
12
Year of publication
1997
Pages
2051 - 2055
Database
ISI
SICI code
0957-4166(1997)8:12<2051:AIPFTL>2.0.ZU;2-R
Abstract
An improved procedure for the kinetic resolution of endo-endo-cis-bicy clo[3.3.0]octane-2,6-diol rac-1 by transesterification with vinyl acet ate catalysed by lipase from Pseudomonas cepacia in an organic solvent which yields both enantiomers with an enantiomeric excess of > 95% is described. The configuration at both stereogenic centres bearing hydr oxy groups has been inverted by treatment of the corresponding mesylat es with caesium acetate in the presence of 18-crown-6 to afford, after deacetylation, the corresponding enantiomerically pure diastereoisome ric exo-exo-cis-diols. (C) 1997 Elsevier Science Ltd.