Catalytic asymmetric alkynylation of alpha-imino ester: a versatile approach to optically active unnatural alpha-amino acid derivatives.
The catalytic asymmetric introduction of alkynyl functionality to alpha-amino acid derivatives was realized by the direct addition of terminal alkynes to alpha-imino ester in the presence of chiral Cu(I) complex under mild reaction conditions. Owing to the rich chemistry to which alkyne can be subjected, the present system provides a remarkably versatile tool for the construction of optically active alpha-amino acid derivatives. Good yields and enantiomeric excess values were achieved with an array of terminal alkynes and challenging, biologically active, unnatural alpha-amino acid derivatives could be conveniently obtained.
Ji
Jian-Xin
JX
Open Laboratory of Chirotechnology, Institute of Molecular Technology for Drug Discovery and Synthesis, and Department of Applied Biology and Chemical Technology, Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
Wu
Jing
J
Chan
Albert S C
AS
D000480:Alkynes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry*; D004952:Esters; D007098:Imino Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy
D000480:Alkynes; D000596:Amino Acids; D004952:Esters; D007098:Imino Acids; D003300:Copper