Diels-Alder reaction of cyclopentadienone acetal with pyrrole and indole

Sota Sato, Tomoko Fujino, Hiroyuki Isobe, Eiichi Nakamura

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    Diels-Alder reactions of a cyclopentadienone acetal with aromatic heterocycles, such as pyrrole or indole, took place with the latter acting as a 2π dienophile. The reaction gave a polycyclic heterocycle in good yield regioselectively. Analysis of the frontier molecular orbitals showed that inverse electron demand interactions control the regioselectivity.

    Original languageEnglish
    Pages (from-to)1288-1292
    Number of pages5
    JournalBulletin of the Chemical Society of Japan
    Volume79
    Issue number8
    DOIs
    Publication statusPublished - 2006 Nov 10

    ASJC Scopus subject areas

    • Chemistry(all)

    Fingerprint Dive into the research topics of 'Diels-Alder reaction of cyclopentadienone acetal with pyrrole and indole'. Together they form a unique fingerprint.

  • Cite this