Highly diastereo- and enantioselective Cu-catalyzed [3 + 3] cycloaddition of propargyl esters with cyclic enamines toward chiral bicyclo[n.3.1] frameworks.
A new Cu-catalyzed asymmetric [3 + 3] cycloaddition of propargyl esters with cyclic enamines is reported. With a combination of Cu(OAc)(2)·H(2)O and a chiral tridentate ferrocenyl-P,N,N ligand as the catalyst, perfect endo selectivities (endo/exo > 98/2) and excellent enantioselectivities (up to 98% ee) for endo cycloadducts were achieved under mild conditions. This method provides a simple and efficient approach for the synthesis of optically active bicyclo[n.3.1] frameworks.
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Cheng
C
Zhang
Xin-Hu
XH
Hu
Ya-Hui
YH
Wang
Zhuo
Z
Zheng
Jie
J
Xu
Xiang-Ping
XP
Hu
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D010293:Pargyline / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D004952:Esters; D003300:Copper; D010293:Pargyline