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Synfacts 2006(5): 0470-0470  
DOI: 10.1055/s-2006-934431
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ferrocene-Based Secondary Alcohols via Asymmetric Hydrogenation

Contributor(s): Hisashi Yamamoto, Matthew Boxer
W. Lam, S. H. L. Kok, T. T.-L. Au-Yeung, J. Wu, H. Cheung, F. Lam, C. Yeung, A. S. C. Chan*
The Hong Kong Polytechnic University, Hong Kong, P. R. of China
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

In the effort to synthesize Ugi’s amine, Chan and coworkers decided to apply Noyori-type rhodium reduction on ferrocenyl ketones to overcome the problems normally associated with this synthesis. As the authors mentioned, the use of a CBS-reduction protocol has been utilized for this synthesis, but a very high catalyst loading is needed (30-60 mol%), making it unattractive for large-scale applications. While the product shown is the methyl-substituted alcohol, aryl-substituted ketones were shown to be viable substrates giving products with >89% ee.