Formation of medium-sized nitrogen heterocycles from gamma-silyloxy-gamma-lactams.
Nitrogen heterocycles can be prepared by performing ring-expansion reactions of gamma-silyloxy-gamma-lactams, which are available by the annulation reactions of allylic silanes. Nucleophilic substitution of the annulation products and subsequent translactamization of nitrogen-tethered gamma-lactams provide six-, seven-, and eight-membered ring lactams. An enantiomerically enriched delta-lactam formed from this method was elaborated to form the hydroxypiperidine core structure of the pseudodistomin alkaloids.
Leonard
Nicholas M
NM
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D012833:Siloxanes / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D006571:Heterocyclic Compounds; D007769:Lactams; D010880:Piperidines; D012821:Silanes; D012833:Siloxanes; C449039:pseudodistomin C; D009584:Nitrogen