Copper-catalyzed amine-alkyne-alkyne addition reaction: an efficient method for the synthesis of gamma,delta-alkynyl-beta-amino acid derivatives.
A simple and efficient method for the synthesis of gamma,delta-alkynyl-beta-amino acid derivatives by a copper-catalyzed three-component amine-alkyne-alkyne addition reaction was developed. Various gamma,delta-alkynyl-beta-amino acid derivatives were synthesized in moderate to good yields in one step. With chiral prolinol derivatives employed as the amine component, excellent diastereoselectivities (up to >99:1 diastereomeric ratio (dr)) were obtained. The scope of the reaction and further transformations of the resulting amino acid derivatives, such as deprotection and cyclization are also described.
Zhou
Lei
L
Department of Chemistry, McGill University, Montreal, QC, H3A 2K6, Canada.
Shuai
Qi
Q
Jiang
Huan-feng
HF
Li
Chao-Jun
CJ
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D013237:Stereoisomerism
D000480:Alkynes; D000588:Amines; D000596:Amino Acids; D003300:Copper