SYNTHESIS OF ENANTIOMERICALLY PURE 4-ACETOXY-2-FLUORO-2-CYCLOPENTEN-1-ONE

Authors
SATO M HIROKAWA T HATTORI H TOYOTA A KANEKO C
Citation
M. Sato et al., SYNTHESIS OF ENANTIOMERICALLY PURE 4-ACETOXY-2-FLUORO-2-CYCLOPENTEN-1-ONE, Tetrahedron : asymmetry, 5(6), 1994, pp. 975-980
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
6
Year of publication
1994
Pages
975 - 980
Database
ISI
SICI code
0957-4166(1994)5:6<975:SOEP4>2.0.ZU;2-L
Abstract
Addition of molecular fluorine to cis-2-cyclopentene-1,4-diol gave the cis-anti adduct stereoselectively. This meso diol was dissymmetrized by means of acetylation under lipase catalysis to afford the monoaceta te with a high enatiomeric purity. Oxidation of the monoacetate follow ed by elimination of hydrogen fluoride under basic conditions furnishe d the titled compound which is an attractive building block for chiral fluorinated molecules.