Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 31, Pages 7034-7038Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402884
Keywords
Asymmetric synthesis; Hydrogenation; Reduction; Asymmetric transfer hydrogenation; Amines; Sulfinylimines
Categories
Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CONSOLIDER INGENIO 2010, CSD2007-00006, CTQ2007-65218, CTQ2011-24151]
- Generalitat Valenciana [PROMETEO/2009/039]
- Generalitat Valenciana (FEDER)
- Spanish Ministerio de Educacion [AP-2008-00989]
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Microwave irradiation has considerably enhanced the efficiency of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines in isopropyl alcohol catalyzed by a ruthenium complex bearing the achiral ligand 2-amino-2-methylpropan-1-ol. In addition to shortening reaction times for the transfer hydrogenation processes to only 30 min, the amounts of ruthenium catalyst and isopropyl alcohol can be consider-ably reduced in comparison with our previous procedure assisted by conventional heating, which diminishes the environmental impact of this new protocol. This methodology can be applied to aromatic, heteroaromatic and aliphatic N-(tertbutylsulfinyl)ketimines, leading, after desulfinylation, to the expected primary amines in excellent yields and with enantiomeric excesses of up to 96%.
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