Unusual regioselective intramolecular Diels-Alder reaction forming tricyclo[4.3.1.0(3,7)]decane system.
The intramoleculae Diels-Alder reaction of cyclohexenone having an unsaturated ester side chain afforded tricyclo[4.3.1.0(3,7)]decanone in both a regio- and stereoselective manner under TMSCl-NEt(3)-ZnBr(2) conditions. Unexpectedly, the regiochemical control was against the conventional orbital requirement.
Takasu
Kiyosei
K
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Mizutani
Sayaka
S
Ihara
Masataka
M