title: Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems.
abstract: Acid treatment of densely substituted 2-silyl-1,2-dihydropyridines provides a new and convenient entry to reactive azomethine ylides that can (1) be protonated and reduced with high stereoselectivity to give piperidines, (2) participate in [3 + 2] dipolar cycloaddition to give tropanes, and (3) undergo a Nazarov-like 6-π electrocyclization that upon reduction give 2-azabicyclo[3.1.0] systems.
authors: Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
authors: Michael A
authors: MA
authors: Ischay
authors: Michael K
authors: MK
authors: Takase
authors: Robert G
authors: RG
authors: Bergman
authors: Jonathan A
authors: JA
authors: Ellman
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001372:Aza Compounds; D001391:Azo Compounds; D001643:Bridged Bicyclo Compounds; D010880:Piperidines; D013882:Thiosemicarbazones; D014326:Tropanes; C512188:azomethine
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