title: Copper-Mediated [3+2] Annulation of 3-N-Hydroxyallylamines with Nitrosoarenes.
abstract: Cu-mediated annulations of N-hydroxyallylamines with nitrosoarenes proceed through unprecedented formal [3+2] cycloadditions of N-hydroxyaminoallyl radicals with nitrosoarenes. Our mechanistic analysis opposes a 5-endo-trig cyclization involved in the final ring-closure step. To manifest the reaction utility, chemical elaborations of resulting isoxazolidinyl products into 2- or 3-substituted quinoline N-oxides and acyclic 1,3-diamino-2-ols are also described.
authors.affiliation: Department of Chemistry, National Tsing-Hua University, 101, Sec. 2, Kuang-Fu Rd., Hsinchu, 30043, Taiwan, P.R. China.
authors.forename: Satish
authors.initials: S
authors.lastname: Ghorpade
authors.affiliation: Department of Chemistry, National Tsing-Hua University, 101, Sec. 2, Kuang-Fu Rd., Hsinchu, 30043, Taiwan, P.R. China.
authors.forename: Prakash D
authors.initials: PD
authors.lastname: Jadhav
authors.affiliation: Department of Chemistry, National Tsing-Hua University, 101, Sec. 2, Kuang-Fu Rd., Hsinchu, 30043, Taiwan, P.R. China. rsliu@mx.nthu.edu.tw.
authors.forename: Rai-Shung
authors.initials: RS
authors.lastname: Liu
keywords: annulation; copper; nitrosoarenes; oxidants; radicals