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Updated: Feb 19, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
A Three-Component Enantioselective Cyclization Reaction Catalyzed by an Unnatural Amino Acid Derivative
María de Gracia Retamosa1, Andrea Ruiz-Olalla1, Tamara Bello1
1Departamento de Química Orgánica I and Centro de Innovación en Química Avanzada (ORFEO-CINQA), University of the Basque Country (UPV/EHU) and Donostia International Physics Center (DIPC), P° Manuel Lardizabal 3, 20018, Donostia/San Sebastián, Spain.
Abstract:
A new diastereo- and enantioselective three-component cyclization reaction is described. The reaction takes place between a ketone, a carboxylic acid, and a nitroalkene to yield a bicyclic octahydro-2H-indol-2-one scaffold possessing three chiral centers. This reaction involves a rearrangement of the nitro group under simple thermal conditions. A plausible mechanism is proposed for this new reaction based on DFT calculations and isotope-labeling experiments. A new concise enantioselective synthesis of the alkaloid (+)-pancracine is presented as an example of the potential of this novel organocatalytic cyclization reaction in the synthesis of natural products.
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