☆ 4.5 Article

Microwave-Enhanced Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl)imines

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Volume 2014, Issue 31, Pages 7034-7038

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/ejoc.201402884

Keywords

Asymmetric synthesis; Hydrogenation; Reduction; Asymmetric transfer hydrogenation; Amines; Sulfinylimines

Categories

Chemistry, Organic

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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Abstract

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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