Related Experiment Video
Updated: Dec 28, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Combined Enzyme- and Transition Metal-Catalyzed Strategy for the Enantioselective Syntheses of Nitrogen Heterocycles:
Donald R Deardorff1, Scott W Niman1, Mark I Paulsen1
1Department of Chemistry, Occidental College, 1600 Campus Rd. M-5, Los Angeles, California 90041, United States.
Abstract:
The enantioselective syntheses of (-)-coniine, DAB-1, and nectrisine have been developed, utilizing a complementary strategy of enzyme- and transition metal-catalyzed reactions. The initial stereocenter was set with >99% enantioselectivity via an enzyme-catalyzed hydrocyanation reaction. Substrate incompatibilities with the natural enzyme were overcome by tactical utilization of ruthenium-catalyzed olefin metathesis to functionalize an enzyme-derived (R)-allylic fragment. The piperidine and pyrrolidine alkaloid natural products were obtained by a route that leveraged regio- and stereoselective palladium-catalyzed 1,3-substitutive reactions.
More Related Videos
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

