Diastereoselective Fluorocyclopropanation of Chiral Allylic Alcohols Using an α-Fluoroiodomethylzinc Carbenoid.

Org Lett

Center in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montreal, P.O. Box 6128, Station Downtown, Montreal, Quebec Canada , H3C 3J7.

Published: September 2015

Chiral fluorocyclopropyl carbinols were synthesized in high diastereoselectivities via a zinc mediated cyclopropanation reaction, using sec-allylic alcohols as simple building blocks. An enantioselective version of this transformation was achieved through in situ formation of chiral allylic zinc sec-alkoxides from the requisite aldehydes using Walsh's protocol.

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http://dx.doi.org/10.1021/acs.orglett.5b02097DOI Listing

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