title: Skeletal Rearrangement in the ZnII-Catalyzed [4+2]-Annulation of Disubstituted N-Hydroxy Allenylamines with Nitrosoarenes to Yield Substituted 1,2-Oxazinan-3-one Derivatives.
abstract: This work reports zinc-catalyzed [4+2]-annulation reactions of disubstituted N-hydroxy allenylamines with nitrosoarenes to afford substituted 1,2-oxazinan-3-ones with a skeletal rearrangement. This annulation is applicable to a reasonable scope of allenylamines and nitrosoarenes. Our control experiments indicate that nitrosobenzene can also implement this annulation through a radical annulation path, but with poor efficiency. Zn(OTf)2or AgOTf greatly improves the efficiency of this [4+2]-annulation; the effect of these metal species is discussed in detail.
authors.affiliation: Department of Chemistry, National Tsing-Hua University, 101, Sec. 2, Kuang-Fu Rd., Hsinchu, 3003, Taiwan, Republic of China.
authors.forename: Pankaj
authors.initials: P
authors.lastname: Sharma
authors.affiliation: Department of Chemistry, National Tsing-Hua University, 101, Sec. 2, Kuang-Fu Rd., Hsinchu, 3003, Taiwan, Republic of China. rsliu@mx.nthu.edu.tw.
authors.forename: Rai-Shung
authors.initials: RS
authors.lastname: Liu
keywords: 1,2-oxazinan-3-ones; [4+2]-annulation; nitrosoarenes; radical annulation; zinc catalysis