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.
Department of Chemistry, McGill University, Montreal, QC, H3A 2K6, Canada.
Lei
L
Zhou
Qi
Q
Shuai
Huan-feng
HF
Jiang
Chao-Jun
CJ
Li
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