Cyclic aldimines as superior electrophiles for Cu-catalyzed decarboxylative Mannich reaction of β-ketoacids with a broad scope and high enantioselectivity.
A novel Cu-catalyzed enantioselective decarboxylative Mannich reaction of cyclic aldimines with β-ketoacids is described. The cyclic structure of these aldimines, in which the C═N bond is constrained in the Z geometry, appears to be important, allowing Mannich condensation to proceed in high yields with excellent enantioselectivities. A chiral chroman-4-amine was synthesized from the decarboxylative Mannich product in several steps without loss of enantioselectivity.
Department of Chemistry, Key Laboratory of Systems Bioengineering (the Ministry of Education), Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. of China.
Heng-Xia
HX
Zhang
Jing
J
Nie
Hua
H
Cai
Jun-An
JA
Ma
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007651:Keto Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D002839:Chromans; D007097:Imines; D007651:Keto Acids; C000591879:chroman-4-amine; D003300:Copper