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Microwave‐Enhanced Asymmetric Transfer Hydrogenation of N ‐( tert ‐Butylsulfinyl)imines
Author(s) -
Pablo Óscar,
Guijarro David,
Yus Miguel
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402884
Subject(s) - chemistry , ruthenium , transfer hydrogenation , isopropyl alcohol , catalysis , alcohol , enantiomer , microwave irradiation , enantiomeric excess , isopropyl , ligand (biochemistry) , combinatorial chemistry , enantioselective synthesis , organic chemistry , medicinal chemistry , receptor , biochemistry
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 considerably 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 ‐( tert ‐butylsulfinyl)ketimines, leading, after desulfinylation, to the expected primary amines in excellent yields and with enantiomeric excesses of up to 96 %.