Computational Studies of Chiral Hydroxyl Carboxylic Acids: The Allylboration of Aldehydes
Open Access
- 4 December 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (23), 15449-15456
- https://doi.org/10.1021/acs.joc.0c02226
Abstract
The mechanism of the asymmetric BINOL-derived hydroxyl carboxylic acid catalyzed allylboration of benzaldehyde was investigated using density functional theory calculations. A new reaction model is proposed, and the roles of the two Bronsted acidic sites of the catalyst elucidated. Catalyst distortion was found to be a key factor in determining stereoselectivity. The flexibility of the hydroxyl carboxylic acid catalyst leads to significant differences in the mechanism and origins of selectivity compared to the equivalent phosphoric acid catalyzed reaction.Funding Information
- Engineering and Physical Sciences Research Council
- University of Bath
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