title: Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines.
abstract: Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines were developed. The reactions between diversely substituted C,N-cyclic azomethine imines and aldehydes proceeded smoothly in the presence of chiral prolinol silyl ether catalyst and gave the C-1-substituted tetrahydroisoquinolines in a highly stereoselective manner. These tetrahydroisoquinolines could be efficiently transformed to several other useful polycyclic frameworks.
authors.affiliation: Allan H. Conney Laboratory for Anticancer Research, Guangdong University of Technology, Guang Dong 510006 (P.R. China); Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691.
authors.forename: Wenjun
authors.initials: W
authors.lastname: Li
authors.forename: Qianfa
authors.initials: Q
authors.lastname: Jia
authors.forename: Zhiyun
authors.initials: Z
authors.lastname: Du
authors.forename: Kun
authors.initials: K
authors.lastname: Zhang
authors.forename: Jian
authors.initials: J
authors.lastname: Wang
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis / Q000737:chemistry; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000588:Amines; D001391:Azo Compounds; D006571:Heterocyclic Compounds; D007097:Imines; D044005:Tetrahydroisoquinolines; D013882:Thiosemicarbazones; C512188:azomethine
keywords: asymmetric synthesis; cycloadditions; enamines; heterocycles; tetrahydroisoquinoline