Issue 20, 2022

Visible-light enabled synthesis of cyclopropane-fused indolines via dearomatization of indoles

Abstract

An efficient synthesis of methylene-unsubstituted cyclopropane-fused indolines via photoredox catalyzed dearomative cyclopropanation of indole derivatives was developed. A broad range of indoles bearing a variety of functional groups were compatible with these mild conditions, affording the products in moderate to excellent yields. Asymmetric cyclopropanation was also realized with the assistance of a chiral auxiliary in good yield with excellent diastereoselectivity, followed by the removal of the auxiliary to give enantioenriched alcohol. The 5 mmol scale reaction and derivatizations of the products were successfully carried out to demonstrate the synthetic value of this reaction.

Graphical abstract: Visible-light enabled synthesis of cyclopropane-fused indolines via dearomatization of indoles

Supplementary files

Article information

Article type
Research Article
Submitted
20 Jul 2022
Accepted
25 Aug 2022
First published
31 Aug 2022

Org. Chem. Front., 2022,9, 5463-5468

Visible-light enabled synthesis of cyclopropane-fused indolines via dearomatization of indoles

X. Huang, Y. Cheng and S. You, Org. Chem. Front., 2022, 9, 5463 DOI: 10.1039/D2QO01174C

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