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Enantioselective Merger of Aminocatalysis with π‐Lewis Acid Metal Catalysis: Asymmetric Preparation of Carbo‐ and Heterocycles
Author(s) -
Praveen Chandrasekaran,
Montaignac Benjamin,
Vitale Maxime R.,
RatovelomananaVidal Virginie,
Michelet Véronique
Publication year - 2013
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201300313
Subject(s) - enantioselective synthesis , stereocenter , chemistry , indane , catalysis , pyrrolidine , organic chemistry , combinatorial chemistry
The metallo‐organocatalyzed enantioselective synthesis of various five‐membered carbo‐ and heterocyclic structures through the merger of aminocatalysis with the catalytic indium(III) or copper(I) activation of α‐disubstituted formyl alkynes is described. The use of indium trichloride associated with the (R)‐1,1′‐bis‐(2‐naphthylamine) ligand led to encouraging results with up to 85:15 enantiomeric ratio. After a careful examination of several other strategies, the best synergic catalytic system, which combines a chiral copper(I) complex with cyclohexylamine, afforded the enantioselective preparations of cyclopentane, indane, and pyrrolidine scaffolds with moderate to excellent control of the all‐carbon quaternary stereogenic centers created through such cyclization processes.