Wang Q, Huang W, Yuan H, Cai Q, Chen L, Lv H, * Zhang X. * Wuhan University, P. R. of China
Rhodium-Catalyzed Enantioselective Hydrogenation of Tetrasubstituted α-Acetoxy β-Enamido Esters: A New Approach to Chiral α-Hydroxy-β-amino Acid Derivatives.
J. Am. Chem. Soc. 2014;
136: 16120-16123
Key words
hydrogenation - α-hydroxy-β-amino acids - rhodium
Significance
Lv, Zhang and colleagues present a rhodium-catalyzed asymmetric hydrogenation of α-acetoxy β-enamido esters. A series of chiral α-hydroxy-β-amino acid derivatives were prepared in high yields (up to 98%) with excellent enantioselectivities (up to 97% ee).
Comment
[Rh(nbd)(Sc,Rp)-DuanPhos]BF4 is found to be an effective catalyst for the enantioselective hydrogenation of tetrasubstituted enamides. The synthetic utility of this method is demonstrated by the synthesis of biologically important molecules.
