M. Sakamoto, M. Nagano, Yoko Suzuki
Jan 15, 1996
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron
Abstract
Abstract Inverse type Diels-Alder reactions of ethyl (E)-3-(1,3-benzothiazol-2-yl)-3-cyanopropenoate (2) as 1-aza-1,3-butadiene are described. The diene (2), bearing electron-withdrawing ester group at diene 4-position, reacts with electron-rich dienophiles (3a-d) under extremely mild conditions to give corresponding cycloadducts (4a-d) with regio- and endo-selectivities. Treatment of 2 with electron-donating allyl alcohols (6a-d) causes tandem transesterification and intramolecular cycloaddition to afford cis-fused polycyclic systems (7a-d) in a single step.