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Synfacts 2010(6): 0675-0675  
DOI: 10.1055/s-0029-1219978
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Biphosphorous Ligands for Rhodium-Catalyzed Asymmetric Hydrogenation

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
W. Tang*, A. G. Capacci, A. White, S. Ma, S. Rodriguez, B. Qu, J. Savoie, N. D. Patel, X. Wei, N. Haddad, N. Grinberg, N. K. Yee, D. Krishnamurthy, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, USA
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Publikationsdatum:
20. Mai 2010 (online)

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Significance

Chiral 1,1-biphosphorous ligands have gained increased attention in recent years. However, some of these ligands possess a number of drawbacks, such as the necessity of preparative HPLC separation, availability of only one enantiomer, issues with handling or stability. The authors have developed a new class of operationally convenient 2-phosphino-2,3-dihydrobenzo-[d][1,3]oxaphosphole ligands, which demonstrated excellent performance in asymmetric hydrogenation of α-(acylamino)acrylic acid derivatives as well as both (E)- and (Z)-β-(acylamino)acrylates. For the hydrogenation of the latter ones, limited success has been previously achieved.