Synthesis of optically active gem-difluorocyclopropanes through a chemo-enzymatic reaction strategy |
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Authors: | Toshiyuki Itoh Nanae Ishida Shuichi Hayase |
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Institution: | a Department of Materials Science, Faculty of Engineering, Tottori University, Tottori 680-8552, Japan b Department of Science Education, Graduate School of Okayama University, Okayama 700-8530, Japan |
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Abstract: | The synthesis of a chiral difluorocyclopropane building block has been accomplished using lipase-catalyzed reaction; the prochiral diacetate of cis-1,3-bishydroxymethyl-2,2-difluorocyclopropane was converted to the corresponding chiral monoacetate by the Alcaligenes lipase (lipase QL)-catalyzed hydrolysis with >99% enantiomeric excess. Enantiomerically pure trans-1,3-bishydroxymethyl-2,2-difluorocyclopropane was also obtained through the Pseudomonas cepacia SL-25 lipase (lipase SL)-catalyzed reaction. The synthesis of the chiral trans,trans-bis-gem-difluorocyclopropane derivatives has been accomplished using the same lipase technology; trans,trans-1,6-bishydroxymethyl-2,2,5,5-tetrafluorobicyclopropane was obtained in optically active form using the lipase SL-catalyzed hydrolysis of the corresponding diacetate. |
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Keywords: | gem-Difluorocyclopropane Lipase-catalyzed reaction Asymmetric synthesis |
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