Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 33, Pages 7339-7342Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403180
Keywords
Alkaloids; Imines; Reduction; Organocatalysis; Lewis bases
Categories
Funding
- Fundacao para a Ciencia e a Tecnologia (FCT) [SFRH/BD/61913/2009]
- FCT [PEst-OE/QUI/UI0619/2011]
- Fundacao para a Ciencia e a Tecnologia [RECI/BBB-BQB/0230/2012]
- Universita degli Studi di Milano
- Fundação para a Ciência e a Tecnologia [SFRH/BD/61913/2009] Funding Source: FCT
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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.
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