Synthesis of optically active bisdifluorocyclopropanes through a chemo-enzymatic reaction strategy

The first synthesis of bisdifluorocyclopropane derivatives has been accomplished via a chemo-enzymatic reaction strategy; ( E)- or ( Z)-3-tributylstannyl-2-propenols were prepared and their conversion led to the ( trans,trans)- and ( cis,cis)-bisdifluorocyclopropanes. The subsequent lipase-catalyzed...

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Published inTetrahedron letters Vol. 40; no. 31; pp. 5739 - 5742
Main Authors Mitsukura, Koichi, Korekiyo, Satoshi, Itoh, Toshiyuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.07.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,3-DIENES
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Summary:The first synthesis of bisdifluorocyclopropane derivatives has been accomplished via a chemo-enzymatic reaction strategy; ( E)- or ( Z)-3-tributylstannyl-2-propenols were prepared and their conversion led to the ( trans,trans)- and ( cis,cis)-bisdifluorocyclopropanes. The subsequent lipase-catalyzed reaction efficiently afforded optically active ( trans,trans)-2,2,5,5-tetrafluoro-1,6-bis(hydroxymethyl)bicyclopropane. The first synthesis of optically active bisdifluorocyclopropanes has been accomplished through the chemical-enzymatic hybrid reaction methodology.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01088-6