Abstract
A one-step catalytic and diastereoselective method for the synthesis of aziridines possessing multiple chiral substitutions by radical aminotrifluoromethylation of alkenes has been developed for the first time. The reaction utilizes a Cu(i)/l-proline complex as a catalyst and a chiral sulfinamide group performs the role of nucleophile and chiral directing group. This synthetic strategy provides one-step access to a wide variety of substituted aziridines with good chemical yield, excellent diastereoselectivity and broad functional group tolerance. A possible reaction mechanism is proposed based on DFT calculations. The method should be useful for the rapid synthesis of chiral CF3-containing building blocks and novel drug molecules.
Original language | English |
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Pages (from-to) | 3132-3136 |
Number of pages | 5 |
Journal | Organic Chemistry Frontiers |
Volume | 7 |
Issue number | 20 |
DOIs | |
Publication status | Published - 21 Oct 2020 |
ASJC Scopus subject areas
- Organic Chemistry