Asymmetric synthesis of tetrahydroquinolines through a [3+2] cycloaddition controlled by dienamine catalysis.
A dienamine-mediated enantioselective 1,3-dipolar cycloaddition catalyzed by a chiral prolinol silyl ether catalyst has been developed. Removal of the benzamide group of the intermediates could furnish chiral C-1 substituted tetrahydroisoquinolines (see scheme) in high yields and excellent stereoselectivities.
Allan H. Conney Laboratory for Anticancer Research, Guangdong University of Technology, Guang Dong, 510006 (China); Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691.
Wenjun
W
Li
Jia
J
Wei
Qianfa
Q
Jia
Zhiyun
Z
Du
Kun
K
Zhang
Jian
J
Wang
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D004987:Ethers / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D004987:Ethers; D011804:Quinolines; C542964:1,2,3,4-tetrahydroquinoline
asymmetric synthesis; azomethine imines; cycloaddition; dienamines; tetrahydroisoquinolines