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A Three‐Component Enantioselective Cyclization Reaction Catalyzed by an Unnatural Amino Acid Derivative
Author(s) -
de Gracia Retamosa María,
RuizOlalla Andrea,
Bello Tamara,
de Cózar Abel,
Cossío Fernando P.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201708952
Subject(s) - enantioselective synthesis , nitroalkene , chemistry , ketone , bicyclic molecule , yield (engineering) , catalysis , derivative (finance) , organocatalysis , reaction mechanism , combinatorial chemistry , stereoisomerism , organic chemistry , stereochemistry , materials science , economics , financial economics , metallurgy
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.