Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 37, Pages 12864-12867Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja507468u
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Funding
- National Institute of General Medical Sciences [R01 GM104534]
- Amgen
- College of Chemistry CheXray (NIH Shared Instrumentation Grant) [S10-RR027172]
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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.
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