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

作者:Zi Weiwei; Wang Yi Ming; Toste F Dean*
来源:Journal of the American Chemical Society, 2014, 136(37): 12864-12867.
DOI:10.1021/ja507468u

摘要

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 enantio-enriched a-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.

  • 出版日期2014-9-17