Stereospecific anti SE2′ fluorination of allenylsilanes: Synthesis of enantioenriched propargylic fluorides

Laurence Carroll, Samantha McCullough, Tom Rees, Timothy D.W. Claridge, Véronique Gouverneur

Research output: Contribution to journalArticlepeer-review

Abstract

The electrophilic fluorodesilylation of enantioenriched allenylsilanes proceeds with efficient transfer of chirality. The silylation-fluorination of propargylic alcohols occurs with overall retention of stereochemistry, a result consistent with a stereospecific anti SE2′ mechanism for the fluorination step.

Original languageEnglish (US)
Pages (from-to)1731-1733
Number of pages3
JournalOrganic and Biomolecular Chemistry
Volume6
Issue number10
DOIs
StatePublished - May 12 2008
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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