A Three‐Component Enantioselective Cyclization Reaction Catalyzed by an Unnatural Amino Acid Derivative

E-ISSN： 1521-3773|57|3|668-672

ISSN： 1433-7851

Source： ANGEWANDTE CHEMIE INTERNATIONAL EDITION, Vol.57, Iss.3, 2018-01, pp. : 668-672

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Abstract

AbstractA 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.