Halogenovinyl Sulfones. 6.(1) Synthesis of Condensed Heterocycles by Diastereoselective Intramolecular Diels-Alder Reactions of Sulfonyl-Substituted Trienes.
作者信息
Takeuchi Hideki, Fujimoto Tetsuya, Hoshino Kenji, Motoyoshiya Jiro, Kakehi Akikazu, Yamamoto Iwao
机构信息
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.
出版信息
J Org Chem. 1998 Oct 16;63(21):7172-7179. doi: 10.1021/jo980181b.
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.
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