214912-01-3Relevant academic research and scientific papers
Halogenovinyl sulfones. 6. Synthesis of condensed heterocycles by diastereoselective intramolecular Diels-Alder reactions of sulfonyl-substituted trienes
Takeuchi, Hideki,Fujimoto, Tetsuya,Hoshino, Kenji,Motoyoshiya, Jiro,Kakehi, Akikazu,Yamamoto, Iwao
, p. 7172 - 7179 (2007/10/03)
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 cisisoindoles 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.
