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Oxidative N‐Heterocyclic Carbene Catalyzed Dearomatization of Indoles to Spirocyclic Indolenines with a Quaternary Carbon Stereocenter
Author(s) -
Bera Srikrishna,
Daniliuc Constantin G.,
Studer Armido
Publication year - 2017
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.201701485
Subject(s) - stereocenter , chemistry , intramolecular force , carbene , moiety , indole test , quaternary carbon , enantioselective synthesis , catalysis , stereochemistry , combinatorial chemistry , organic chemistry
An efficient method for the asymmetric intramolecular dearomatization of indoles by using oxidative N‐heterocyclic carbene catalysis is demonstrated. Valuable optically active spirocyclic indolenines bearing an all‐carbon quaternary stereocenter are obtained in excellent yields and with excellent enantioselectivity. The starting indoles are readily prepared and the reactions proceed through an intramolecular indole 3‐acylation with an in situ generated acyl azolium intermediate to form a spirocyclic ketone moiety.