Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp3)H bondsElectronic supplementary information (ESI) available. CCDC 18338641833865, 18338671833868. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01476k

Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation... A new CC bond formation strategy based on enantioselective radical alkylation of C(sp3)H bonds via Co(ii)-based metalloradical catalysis has been demonstrated for stereoselective synthesis of chiral indolines. The Co(ii)-based system enables activation of aryldiazomethanes as radical precursors at room temperature for enantioselective intramolecular radical alkylation of broad types of CH bonds, constructing 2-substituted indolines in high yields with excellent enantioselectivities. In addition to chemoselectivity and regioselectivity, this Co(ii)-catalyzed alkylation features tolerance to functional groups and compatibility with heteroaryl substrates. Detailed mechanistic studies provide insight into the underlying stepwise radical pathway. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemical Science Royal Society of Chemistry

Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp3)H bondsElectronic supplementary information (ESI) available. CCDC 18338641833865, 18338671833868. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01476k

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Publisher
Royal Society of Chemistry
Copyright
This journal is © The Royal Society of Chemistry
ISSN
2041-6520
D.O.I.
10.1039/c8sc01476k
Publisher site
See Article on Publisher Site

Abstract

A new CC bond formation strategy based on enantioselective radical alkylation of C(sp3)H bonds via Co(ii)-based metalloradical catalysis has been demonstrated for stereoselective synthesis of chiral indolines. The Co(ii)-based system enables activation of aryldiazomethanes as radical precursors at room temperature for enantioselective intramolecular radical alkylation of broad types of CH bonds, constructing 2-substituted indolines in high yields with excellent enantioselectivities. In addition to chemoselectivity and regioselectivity, this Co(ii)-catalyzed alkylation features tolerance to functional groups and compatibility with heteroaryl substrates. Detailed mechanistic studies provide insight into the underlying stepwise radical pathway.

Journal

Chemical ScienceRoyal Society of Chemistry

Published: May 18, 2018

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