title: Highly selective cascade couplings for the syntheses of functionalized piperidinones and bispidines.
abstract: Efficient cascade couplings to synthesize functionalized piperidinones 1 and bispidines 2 and 3 have been developed. Simple modifications to the reaction conditions allow for the highly controlled and selective formation of each compound. In addition, the cis isomer of 1 can be selectively obtained under acidic conditions, while the preparation of the corresponding trans isomer can also be readily realized through a base-catalyzed, dynamic crystallization-driven process.
authors.affiliation: Department of Process Research, Merck Research Laboratories, Rahway, NJ 07065, USA. feng_xu@merck.com
authors.forename: Feng
authors.initials: F
authors.lastname: Xu
authors.forename: Edward
authors.initials: E
authors.lastname: Corley
authors.forename: Jerry A
authors.initials: JA
authors.lastname: Murry
authors.forename: David M
authors.initials: DM
authors.lastname: Tschaen
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003460:Crystallization; D007202:Indicators and Reagents; D008968:Molecular Conformation; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D004364:Pharmaceutical Preparations; D010880:Piperidines; C495809:bispidine