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Highly Enantioselective [3+2] Annulation of Indoles with Quinones to Access Structurally Diverse Benzofuroindolines
Author(s) -
Liu QiongJie,
Zhu Jun,
Song XiangYang,
Wang Lijia,
Wang Sunewang R.,
Tang Yong
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800733
Subject(s) - annulation , enantioselective synthesis , catalysis , molecular sieve , ligand (biochemistry) , chemistry , combinatorial chemistry , hydrate , stereochemistry , organic chemistry , receptor , biochemistry
A facile and efficient method to produce optically pure benzofuroindolines, especially those without 3‐substituents that are susceptible to rearomatization, through [3+2] annulation of indoles with quinones is described. The suitable combination of a BOX ligand Cu II hydrate complex and freshly activated molecular sieves functions to give controllably dynamic release of water, which enables the success of this reaction. This reaction can be performed on a gram scale with only 0.5 mol % catalyst loading.