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Title: Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation
Authors: Burke, Anthony
Barrulas, Pedro
Benaglia, Maurizio
Andrea, Genoni
Editors: Ross, Haymo
Keywords: Organocatálise
Issue Date: 1-Nov-2014
Publisher: Wiley-VCH
Abstract: Picolinamide-cinchona organocatalysts for the successful enantioselective reduction of ketomines were developed. For the first time, a new type of chiral Lewis base, a cationic species, is reported to efficiently organocatalyze the addition of trichlorosilane to imines. Excellent yields with good to high enantioselectivities (up to 91%) were obtained in the reduction of differently substituted substrates. Noteworthy, remarkably high turnover frequencies for the hydrosilylation of imines were observed; the catalyst of choice proved to be active even at a loading of only 1 mol-%. The loading was further reduced to 0.5 mol-%, and for very short reaction times (15 min) very impressive asymmetric catalyst efficiency speed values were reached.
ISSN: 1434-193X
Type: article
Appears in Collections:QUI - Publicações - Artigos em Revistas Internacionais Com Arbitragem Científica

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