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

Author:
Zi, Weiwei, Wang, Yi-Ming, Toste, F. Dean
Source:
Journal of the American Chemical Society 2014 v.136 no.37 pp. 12864-12867
ISSN:
1520-5126
Subject:
alcohols, chemical bonding, enantiomers
Abstract:
An enantioselective fluorination of allylic alcohols under chiral anion phase-transfer conditions is reported. The 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. Mechanistic studies suggest that this transformation proceeds through a concerted enantiodetermining transition state involving both C–F bond formation and C–H bond cleavage.
Agid:
5399454