Abstract
1,1′-Bi-2-naphthol (BINOL)-derived catalysts catalyze the asymmetric propargylation of ketones. Density functional theory (DFT) calculations show that the reaction proceeds via a closed six-membered transition structure (TS) in which the chiral catalyst undergoes an exchange process with the original cyclic boronate ligand. This leads to a Lewis acid type activation mode, not a Brønsted acid process, which accurately predicts the stereochemical outcome observed experimentally.
Original language | English |
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Pages (from-to) | 8796-8801 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 78 |
Issue number | 17 |
DOIs | |
Publication status | Published - 6 Sept 2013 |
ASJC Scopus subject areas
- Organic Chemistry