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Synfacts 2015; 11(1): 0050
DOI: 10.1055/s-0034-1379759
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Enantioselective Hydrogenation of Enamido Esters

Contributor(s):
Hisashi Yamamoto
,
Masahiro Sai
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
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Publication History

Publication Date:
15 December 2014 (online)

 
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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).


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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.


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