Computational Studies of Chiral Hydroxyl Carboxylic Acids: The Allylboration of Aldehydes

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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 Brønsted 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.
Original languageEnglish
Pages (from-to)15449–15456
JournalJournal of Organic Chemistry
Volume85
Issue number23
Early online date23 Nov 2020
DOIs
Publication statusPublished - 4 Dec 2020

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