Aldehyde- and ketone-induced tandem decarboxylation-coupling (Csp(3)-Csp) of natural alpha-amino acids and alkynes.
An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO(2) and H(2)O as the only byproducts. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.
Bi
Hai-Peng
HP
Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A 2K6, Canada.
Teng
Qingfeng
Q
Guan
Min
M
Chen
Wen-Wen
WW
Liang
Yong-Min
YM
Yao
Xiaojun
X
Li
Chao-Jun
CJ
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003653:Decarboxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000447:Aldehydes; D000480:Alkynes; D000596:Amino Acids; D003300:Copper