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Synfacts 2014; 10(8): 0885
DOI: 10.1055/s-0034-1378466
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Hydrogenation of Amino Acids with Rh–MoOx/SiO2

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Heeyoel Baek
Tamura M, Tamura R, Takeda Y, Nakagawa Y, Tomishige K * Tohoku University, Sendai, Japan
Catalytic Hydrogenation of Amino Acids to Amino Alcohols with Complete Retention of Configuration.

Chem. Commun. 2014;
50: 6656-6659
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Further Information

Publication History

Publication Date:
18 July 2014 (online)

 
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Key words

hydrogenation - rhodium - amino acids - heterogeneous catalysis

Significance

Rh–MoOx supported on SiO2 (Rh–MoOx/SiO2) catalyzed the hydrogenation of amino acids with H2SO4 and hydrogen in water under mild conditions to give the corresponding amino alcohols in up to 92.8% yield. The catalyst was ­recovered by centrifugation and reused twice to give l-alaninol without significant loss of catalytic activity.


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Comment

Reducible metal–metal oxide (M–M′Ox) catalysts have been previously developed by the authors and other groups (Y. Nakagawa et al. J. Catal. 2010, 272, 191; S. Koso et al. Chem. Commun. 2009, 2035). The Rh–MoOx/SiO2 catalyst with a Mo/Rh molar ratio of 1:8 afforded the high activity by the synergistic effect between rhodium and MoOx. Almost perfect stereochemical integrity was observed under the reaction conditions.


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