Journal of Organic Chemistry, volume 85, issue 13, pages 8544-8552

Regio- and Diastereoselective Indium-Catalyzed Conia-Ene Reaction of ortho-Alkynyl Diketopiperazines to Access Fused Diketopiperazinoindolines.

Publication type: Journal Article
Publication date: 2020-06-16
scimago Q2
wos Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
An efficient synthesis of diketopiperazinoindolines through an indium-catalyzed intramolecular 5-exo-dig cyclization of ortho-alkynyl diketopiperazines has been reported. The formation of diketopiperazinoindolines proceeds via a regio- and diastereoselective Conia-ene reaction. This synthetic method opens a new door for easy access to functionalized fused diketopiperazinoindolines in high to excellent yields with exclusive Z diastereoselectivity.
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