Related Experiment Video
Updated: May 25, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Kinetic resolution of secondary alcohols using amidine-based catalysts
Ximin Li1, Hui Jiang, Eric W Uffman
1Department of Chemistry, Washington University, One Brookings Drive, St. Louis, Missouri 63130, USA.
Abstract:
Kinetic resolution of racemic alcohols has been traditionally achieved via enzymatic enantioselective esterification and ester hydrolysis. However, there has long been considerable interest in devising nonenzymatic alternative methods for this transformation. Amidine-based catalysts (ABCs), a new class of enantioselective acyl transfer catalysts developed in our group, have demonstrated, inter alia, high efficacy in the kinetic resolution of benzylic, allylic, and propargylic secondary alcohols and 2-substituted cycloalkanols, and thus provide a viable alternative to enzymes.
Related Concept Videos
Acid-Catalyzed Dehydration of Alcohols to Alkenes
Conversion of Alcohols to Alkyl Halides
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

