A Three‐Component Enantioselective Cyclization Reaction Catalyzed by an Unnatural Amino Acid Derivative. (12th December 2017)

• Record Type: Journal Article
• Authors: de Gracia Retamosa, María; Ruiz‐Olalla, Andrea; Bello, Tamara; de Cózar, Abel; Cossío, Fernando P.
• Is Part Of: Angewandte Chemie. Volume 130:Number 3(2018)
• Page Start: 676
• Page End: 680
• Publication Date: 2017-12-12
• Subjects: Asymmetrische Katalyse -- Heterocyclen -- Mehrkomponentenreaktionen -- Organokatalyse -- Synthesemethoden; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201708952
• Languages: English
• ISSNs: 0044-8249

Abstract

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‐2 H ‐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.