Related Experiment Video
Updated: Jul 13, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Regio- and Enantioselective Macrocyclization from Dynamic Imine Formation: Chemo- and Enantioselective Fluorescent
Yifan Mao1, Stephanie Davis1, Lin Pu1
1Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, United States.
Abstract:
The dynamic covalent chemistry of imines is utilized to conduct a regioselective as well as enantioselective synthesis of an unsymmetric (C1) chiral macrocycle from the reaction of an unsymmetric (C1) chiral dialdehyde, (S)-4, that contains a salicylaldehyde unit and a benzaldehyde unit, with lysine, an unsymmetric (C1) chiral diamine. The enantioselectivity is further enhanced in the presence of Zn2+. Compound (S)-4 in combination with Zn2+ is found to be a highly chemoselective as well as enantioselective fluorescent probe for lysine. It can be used to detect specific enantiomers of this amino acid.
Related Concept Videos
Regioselective Formation of Enolates
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
α-Alkylation of Ketones via Enolate Ions
Prochirality
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)