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Updated: Jul 21, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis, resolution, and aldol reactions of a planar-chiral Lewis acid complex
Shih-Yuan Liu1, Ivory D Hills, Gregory C Fu
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Abstract:
The synthesis and resolution of a new planar-chiral Lewis acid complex is described. The compound is applied to asymmetric Mukaiyama aldol reactions, leading to the formation of the desired product with good stereoselectivity. The sense of stereoselection is as predicted by the design, which exploits the ability of the Lewis acid to simultaneously serve as a sigma and a pi acceptor. Mechanistic observations are consistent with rate-determining formation of an aldehyde-Lewis acid complex, followed by rapid nucleophilic addition.
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