Stereoselective Nucleophilic Halogenation at CF3-Substituted Nonclassical Carbocation

Veronika Myronova, Dominique Cahard, Ilan Marek

Research output: Contribution to journalArticlepeer-review

Abstract

CF3-substituted cyclopropyl carbinol derivatives undergo regioselective and diastereoselective nucleophilic halogenation at the quaternary carbon center to provide acyclic products as a single diastereomer. The selectivity of the substitution is rationalized by the formation of a nonclassical cyclopropylcarbinyl cation intermediate, reacting at the most-substituted carbon center. Tertiary alkyl chlorides, bromides, and fluorides adjacent to a stereogenic C-CF3-motif are diastereomerically pure and can be obtained in few catalytic steps from commercially available alkynes.

Original languageEnglish
Pages (from-to)3657-3660
Number of pages4
JournalOrganic Letters
Volume26
Issue number17
DOIs
StatePublished - 3 May 2024

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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