Diels-Alder reaction of cyclopentadienone acetal with pyrrole and indole

Sota Sato; Tomoko Fujino; Hiroyuki Isobe; Eiichi Nakamura

doi:10.1246/bcsj.79.1288

Diels-Alder reaction of cyclopentadienone acetal with pyrrole and indole

Sota Sato, Tomoko Fujino, Hiroyuki Isobe, Eiichi Nakamura

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1288-1292
Number of pages	5
Journal	Bulletin of the Chemical Society of Japan
Volume	79
Issue number	8
DOIs	https://doi.org/10.1246/bcsj.79.1288
Publication status	Published - 2006 Nov 10

ASJC Scopus subject areas

Chemistry(all)

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10.1246/bcsj.79.1288

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Sato, S., Fujino, T., Isobe, H., & Nakamura, E. (2006). Diels-Alder reaction of cyclopentadienone acetal with pyrrole and indole. Bulletin of the Chemical Society of Japan, 79(8), 1288-1292. https://doi.org/10.1246/bcsj.79.1288

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