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An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols

Weiwei Zi, Yi-Ming Wang and F. Dean Toste*

*Department of Chemistry, University of California, Berkeley, California 94720, United States, Email: fdtosteberkeley.edu

W. Zi, Y.-M. Wang, F. D. Toste, J. Am. Chem. Soc., 2014, 136, 12864-12867.

DOI: 10.1021/ja507468u (free Supporting Information)



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Abstract

In an enantioselective fluorination of allylic alcohols under chiral anion phase-transfer conditions, an in situ generation of a directing group proved crucial for achieving effective enantiocontrol. In the presence of such a directing group, a range of acyclic substrates underwent fluorination to afford highly enantioenriched α-fluoro homoallylic alcohols.

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Key Words

Fluorination, Selectfluor


ID: J48-Y2014