O-alkenyl hydroxylamines: a new concept for cyclofunctionalization.
[reaction: see text] Treatment of O-homoallylhydroxylamines with palladium(II) and copper(II) in the presence of a base, methanol, and carbon monoxide results in the formation of isooxazolidines. An electron-withdrawing group on the hydroxylamine nitrogen is essential. When carbamate groups are used the products are formed exclusively as their cis isomers.
Bates
Roderick W
RW
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Vibahavadi-Rangsit Highway, Laksi, Bangkok 10210, Thailand. roderick@tubtim.cri.or.th
Sa-Ei
Kanicha
K