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An in situ directing group strategy for chiral anion phase-transfer fluorination of allylic alcohols.

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 ?-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.

SUBMITTER: Zi W

PROVIDER: S-EPMC4183625 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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An in situ directing group strategy for chiral anion phase-transfer fluorination of allylic alcohols.

Zi Weiwei W Wang Yi-Ming YM Toste F Dean FD

Journal of the American Chemical Society 20140909 37

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 bo ...[more]

PMID: 25203796

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