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Synfacts 2006(4): 0364-0364  
DOI: 10.1055/s-2006-934341
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Hydrogenation of Unfunctionalized Alkyl-Substituted Olefins

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. Bell, B. Wüstenberg, S. Kaiser, F. Menges, T. Netscher, A. Pfaltz*
University of Basel, Switzerland
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Publikationsdatum:
24. März 2006 (online)

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Significance

This is a very exciting paper on the hydrogenation of unfunctionalized olefins. Use of bidentate P,N-ligands designed in the Pfaltz group allows for extremely effective hydrogenation under typical conditions. Only 1 mol% of the catalyst is needed and high selectivity (92% ee) is obtained for the cyclohexylalkene hydrocarbon (shown). The importance of this finding is shown by the hydrogenation of two olefins in γ-tocotrienyl acetate giving >98% selectivity for the desired compound.