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Synfacts 2011(1): 0113-0113  
DOI: 10.1055/s-0030-1259145
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Hydrogenation with MCM-41-Supported Pincer Catalysts

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Shaheen M. Sarkar
C. del Pozo, A. Corma, M. Iglesias*, F. Sánchez*
Instituto de Ciencia de Materiales de Madrid, Instituto de Tecnología Química, Valencia and Instituto de Química Orgánica General, Madrid, Spain
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Publication History

Publication Date:
21 December 2010 (online)

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Significance

An MCM-41-supported unsymmetrical, optically active pincer rhodium complex, MCM-Rh, was prepared for the asymmetric hydrogenation of alkenes. Thus, the reaction of (E)-­diethyl 2-benzylidene succinate (1) was carried out with 0.1 mol% Rh of MCM-Rh under hydrogen atmospheric conditions to give 99% ee of (S)-2 in 96% conversion with 7680 h-¹ of TOF. The catalyst was readily recovered by centrifugation and reused four times without loss of catalytic activity. In contrast, the reaction with a homogeneous counterpart homo-Rh afforded 99% ee of (R)-2 with 500 h-¹ of TOF under similar conditions.