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Highly Chemo‐ and Stereoselective Catalyst‐Controlled Allylic C−H Insertion and Cyclopropanation Using Donor/Donor Carbenes
Author(s) -
Zhu Dong,
Chen Lianfen,
Zhang He,
Ma Zhiqiang,
Jiang Huanfeng,
Zhu Shifa
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.201805676
Subject(s) - cyclopropanation , chemoselectivity , intramolecular force , allylic rearrangement , chemistry , cyclopropane , stereoselectivity , medicinal chemistry , catalysis , stereochemistry , migratory insertion , organic chemistry , ring (chemistry)
The highly chemo‐, enantio‐, and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes are reported. The Ru II /Pybox complex selectively catalyzed the intramolecular allylic C−H insertion, providing vinyl‐substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99 % ee . Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane‐fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97 % ee .