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Synfacts 2006(9): 0970-0970  
DOI: 10.1055/s-2006-949250
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

An Orthogonal Self-Assembled Heterogeneous Catalyst for Asymmetric Hydrogenation

Contributor(s): Yasuhiro Uozumi, Takayasu Arakawa
L. Shi, X. Wang, C. A. Sandoval, M. Li, Q. Qi, Z. Li, K. Ding*
Shanghai Institute of Organic Chemistry and Shanghai University, P. R. of China
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

The orthogonal self-assembled heterogeneous catalyst 2 has been developed based on hydrogen bonding and ligand-to-metal coordination interactions and was used in the asymmetric hydrogenation. The heterogeneous catalyst 2 was prepared from ligand 1 (2 mol equiv) and [Rh(cod)2]BF4 (0.007 M) in CH2Cl2. The asymmetric hydrogenation of (Z)-methyl-2-acetyl­amino-2-butenoate (3) was carried out in toluene under H2 pressure in the presence of insoluble catalyst 2 to give 4 (96% ee) with a TOF of 180 h-1.