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Updated: Nov 29, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Computational Studies of Chiral Hydroxyl Carboxylic Acids: The Allylboration of Aldehydes
Elliot H E Farrar1, Matthew N Grayson1
1Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, U.K.
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.
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