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

Weiwei Zi | Zendy; Yiming Wang | Zendy; F. Dean Toste | Zendy

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

Author(s) -

Weiwei Zi,

Yiming Wang,

F. Dean Toste

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja507468u

Subject(s) - chemistry , allylic rearrangement , enantioselective synthesis , bond cleavage , in situ , ion , group (periodic table) , functional group , cleavage (geology) , leaving group , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , catalysis , polymer , geotechnical engineering , fracture (geology) , engineering

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.

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