Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles

Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(η3-methallyl)2(cod) and a trans-chela...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-05, Vol.133 (19), p.7312-7315
Main Authors: Kuwano, Ryoichi, Kameyama, Nao, Ikeda, Ryuhei
Format: Article
Language:English
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Summary:Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(η3-methallyl)2(cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered aromatic rings containing two or more heteroatoms.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja201543h