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Synfacts 2005(1): 0131-0131  
DOI: 10.1055/s-2005-916013
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Hydrogenation of tert-Alkyl Ketones

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Ohkuma, C. A. Sandoval, R. Srinivasan, Q. Lin, Y. Wei, K. Muñiz, R. Noyori*
Nagoya University, Japan
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

Success with highly hindered tert-alkyl ketones remained an elusive element to the ruthenium-catalyzed hydrogenation reaction. The authors have overcome this problem by replacing the normally used symmetric 1,2-diamine or bipyridine with an unsymmetrical pyridine/NH2 hybrid ligand and ethanol as solvent. The reaction proceeds at room temperature, 1-20 atm with an S/C ratio of 100,000.