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Synfacts 2013; 9(1): 0059
DOI: 10.1055/s-0032-1317784
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ruthenium-Catalyzed Asymmetric Hydrogenation of β‑Ketophosphonates

Contributor(s):
Hisashi Yamamoto
,
Jiajing Tan
Tao X, Li W, Ma X, Li X, Fan W, Zhu L, Xie X, Zhang Z * Shanghai Jiao Tong University and Shanghai Institute of Organic Chemistry, P. R. of China
Enantioselective Hydrogenation of β‑Ketophosphonates with Chiral Ru(II) Catalysts.

J. Org. Chem. 2012;
77: 8401-8409
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

ruthenium - hydrogenation - ketophosphonates

Significance

The current work represents an efficient protocol for the enantioselective hydrogenation of β‑ketophosphonate derivates catalyzed by a ruthenium–(S)-Sunphos complex. Good to excellent enantioselectivity and yield were obtained for a variety of substrates.


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Comment

Hydroxyphosphonate motifs are known to be mimics of hydroxy carboxylic acids or amino acids. Given their medicinal importance, many synthetic methodologies have been developed. The protocol described herein was even used for the reduction of α-substituted β‑ketophosphonates, providing the desired products with good syn diastereoselectivity.


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