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 language | English |
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Pages (from-to) | 3657-3660 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 26 |
Issue number | 17 |
DOIs | |
State | Published - 3 May 2024 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry