Highly Chemo‐ and Stereoselective Catalyst‐Controlled Allylic C−H Insertion and Cyclopropanation Using Donor/Donor Carbenes | Zendy

Zhu Dong | Zendy; Chen Lianfen | Zendy; Zhang He | Zendy; Ma Zhiqiang | Zendy; Jiang Huanfeng | Zendy; Zhu Shifa | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201805676

Subject(s) - cyclopropanation , chemoselectivity , intramolecular force , allylic rearrangement , cyclopropane , chemistry , medicinal chemistry , stereoselectivity , catalysis , stereochemistry , 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 .

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