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 › peer-review

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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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.",

author = "Sota Sato and Tomoko Fujino and Hiroyuki Isobe and Eiichi Nakamura",

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AU - Sato, Sota

AU - Fujino, Tomoko

AU - Isobe, Hiroyuki

AU - Nakamura, Eiichi

PY - 2006/11/10

Y1 - 2006/11/10

N2 - 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.

AB - 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.

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ER -

Diels-Alder reaction of cyclopentadienone acetal with pyrrole and indole

Abstract

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