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Intermolecular Enantioselective Dearomatization Reaction of β‐Naphthol Using meso ‐Aziridine: A Bifunctional In Situ Generated Magnesium Catalyst
Author(s) -
Yang Dongxu,
Wang Linqing,
Han Fengxia,
Li Dan,
Zhao Depeng,
Wang Rui
Publication year - 2015
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.201410257
Subject(s) - enantioselective synthesis , catalysis , bifunctional , chemistry , aziridine , intermolecular force , magnesium , ligand (biochemistry) , in situ , combinatorial chemistry , organic chemistry , molecule , ring (chemistry) , biochemistry , receptor
A direct, facile, and highly diastereo‐ and enantioselective dearomatization reaction of β‐naphthol derivatives with aziridines has been developed for the first time. A newly designed Box–OH ligand was employed for an in situ generated magnesium catalyst and proved to be efficient. The corresponding dearomatization product was transformed into a polycyclic scaffold and polyhydroxylated compound. 1 H NMR studies revealed the activation mode of the dearomatization process of β‐naphthols, and a clear positive nonlinear effect was observed in the reaction, and provides insight into the coordination environment around the Mg II center and the possible active species.