Premium
PyBidine/Copper Catalyst: Asymmetric exo′ ‐Selective [3+2] Cycloaddition using Imino Ester and Electrophilic Indole
Author(s) -
Awata Atsuko,
Arai Takayoshi
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405223
Subject(s) - electrophile , cycloaddition , enantioselective synthesis , nucleophile , chemistry , indole test , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry
Electrophilic indoles having two electron‐withdrawing groups undergo nucleophilic attack at C2 and electrophilic functionalization at C3. This is the first enantioselective formal [3+2] cycloaddition using electrophilic indoles. The PyBidine/Cu catalyst smoothly promoted highly enantio‐ and exo′‐selective [3+2] cycloaddition using imino esters and 3‐nitroindoles. This reaction provides a method for the preparation of diverse and complex chiral pyrroloindoline compounds.