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Synthesis of enantiomerically pure 4-acetoxy-2-fluoro-2-cyclopenten-1-one

✍ Scribed by Masayuki Sato; Taiko Hirokawa; Hanae Hattori; Akemi Toyota; Chikara Kaneko

Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
414 KB
Volume
5
Category
Article
ISSN
0957-4166

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✦ Synopsis

Addition of molecular fluorine to cis-2-cyclopentene-1 ,Cdiol gave the c&anti adduct stereoselectively. This meso diol was dissymmetrized by means of acetylation under lipase catalysis to afford the monoacetate with a high enatiomeric purity. Oxidation of the monoacetate followed by elimination of hydrogen fluoride under basic conditions furnished the titled compound which is an amactive building block for chiral fluorinated molecules.

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