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
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.
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.
