title: Stereodefined N,O-acetals: Pd-catalyzed synthesis from homopropargylic amines and utility in the flexible synthesis of 2,6-substituted piperidines.
abstract: We developed a conceptually new synthetic strategy which exploits the stereochemical information of labile acyclic N,O-acetals. The key to this strategy, chemo- and stereoselective synthesis of N,O-acetals, was achieved by the Pd-catalyzed addition of sulfonyl-protected homopropargylic amines to alkoxyallene. The N,O-acetals generated in this way were combined with Au-catalyzed cycloisomerization to give an access to 2,6-disubstituted piperidines with stereochemical flexibility.
authors.affiliation: Department of Chemistry, Pohang University of Science and Technology, Hyoja-dong San 31, Pohang, Kyungbuk, Republic of Korea 790-784.
authors.forename: Haejin
authors.initials: H
authors.lastname: Kim
authors.forename: Young Ho
authors.initials: YH
authors.lastname: Rhee
mesh_terms: D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000466:Alkadienes; D000480:Alkynes; D000588:Amines; D010880:Piperidines; D010165:Palladium