1383738-80-4Relevant academic research and scientific papers
Enantioselective merger of aminocatalysis with π-Lewis Acid Metal Catalysis: Asymmetric Preparation of Carbo- and Heterocycles
Praveen, Chandrasekaran,Montaignac, Benjamin,Vitale, Maxime R.,Ratovelomanana-Vidal, Virginie,Michelet, Veronique
, p. 2395 - 2404 (2013)
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.
Enantioselective metallo-organocatalyzed preparation of cyclopentanes bearing an all-carbon quaternary stereocenter
Montaignac, Benjamin,Praveen, Chandrasekaran,Vitale, Maxime R.,Michelet, Veronique,Ratovelomanana-Vidal, Virginie
supporting information; experimental part, p. 6559 - 6561 (2012/08/08)
Enantioselective metallo-organocatalyzed carbocyclizations of formyl-alkynes have been developed. The cooperation between aminocatalysis and a chiral copper(i) complex granted access to enantio-enriched cyclopentanes through the challenging formation of all-carbon quaternary stereocenters.
