Halogenovinyl Sulfones. 6.(1) Synthesis of Condensed Heterocycles by Diastereoselective Intramolecular Diels-Alder Reactions of Sulfonyl-Substituted Trienes.
Sulfonyl trienes having a chiral center on the allyl carbon of the diene moiety were prepared from L-amino acid as chiral building blocks. Intramolecular Diels-Alder reaction of the sulfonyl trienes having E-geometry on the diene moiety proceeded on the si-face and exo-selectively to give cis-isoindoles as a sole product in good yields. But using the sulfonyl trienes having Z-geometry on the diene part, the ratio of the diastereomers of the products decreased to about 80:20. The observed stereoselectivity can be explained by calculations with semiempirical and ab initio methods.
Takeuchi
Hideki
H
Department of Functional Polymer Science, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386-8567, Japan, Department of Materials Creation Chemistry, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386-8567, Japan, and Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan.
Fujimoto
Tetsuya
T
Hoshino
Kenji
K
Motoyoshiya
Jiro
J
Kakehi
Akikazu
A
Yamamoto
Iwao
I