A diastereoselective intermolecular heck reaction of 1,3-dioxepins.
A 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.
Nasveschuk
Christopher G
CG
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Frein
Jeffrey D
JD
Jui
Nathan T
NT
Rovis
Tomislav
T
D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004988:Ethers, Cyclic; D010082:Oxepins