ol702294u_si_004.cif (12.52 kB)
A Diastereoselective Intermolecular Heck Reaction of 1,3-Dioxepins
dataset
posted on 2007-11-22, 00:00 authored by Christopher G. Nasveschuk, Jeffrey D. Frein, Nathan T. Jui, Tomislav RovisA highly diastereoselective intermolecular Heck reaction of 1,3-dioxepins is reported. Substitution at both the 2- and 4-positions of the dioxepin
directs the Pd coordination and subsequent olefin insertion to provide the trans-disubstituted adduct in good yield and high diastereoselectivity.
Chemoselective Heck reaction occurs at the dioxepin alkene in the presence of other olefinic functional groups. A labeling study has been
conducted which suggests that the reaction is under kinetic control.