Design of C1-symmetric tridentate ligands for enantioselective dearomative [3 + 2] annulation of indoles with aminocyclopropanes

Hai-Xia Wang, Chun Yang, Bai-Yu Xue, Ming-Sheng Xie (), Yin Tian (), Cheng Peng and Hai-Ming Guo ()
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Hai-Xia Wang: Henan Normal University
Chun Yang: Henan Normal University
Bai-Yu Xue: Henan Normal University
Ming-Sheng Xie: Henan Normal University
Yin Tian: Chengdu University of Traditional Chinese Medicine
Cheng Peng: Chengdu University of Traditional Chinese Medicine
Hai-Ming Guo: Henan Normal University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Chiral polycyclic indolines are widely present in natural products and have become the focus of extensive synthetic efforts. Here, we show the catalytic asymmetric dearomative [3 + 2] annulation of indoles with donor-acceptor aminocyclopropanes to construct tricyclic indolines. Key to the success of the reaction is the rational design of C1-symmetric bifunctional tridentate imidazoline-pyrroloimidazolone pyridine ligand. Under 5 mol% of Ni(OTf)2-ligand complex, diverse tricyclic indolines containing cyclopentamine moieties are obtained in good chemoselectivities, high diastereoselectivities, and excellent enantioselectivities. An unusual cis-configuration ligand is superior to the trans-configuration ligand and the corresponding C2-symmetric tridentate nitrogen ligands in the annulation reaction. Mechanistic studies by control experiments and density functional theory calculations reveal a dual activation manner, where Ni(II) complex activates the aminocyclopropane via coordination with the geminal diester, and imidazolidine NH forms a H-bond with the succinimide moiety.

Date: 2023
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DOI: 10.1038/s41467-023-38059-7

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