S. Fujii, Mayu Nakano, Y. Yamaoka
Jun 3, 2015
Citations
0
Influential Citations
3
Citations
Journal
Tetrahedron Letters
Abstract
Abstract A reaction of N-tosyl cycloalkanecarbaldimines with iodomethyl pivalate was initiated by triethylborane to give pivaloyloxymethylated products bearing 3-iodocycloalkyl groups. Radical addition of pivaloyloxymethyl to imines generates aminyl radicals, which then regioselectively cleave C H bonds at the 3-position of the cycloalkane moieties. The resulting carbon-centered radicals are trapped with iodine. DFT calculations rationalized stereo- and regioselectivity.