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 ဇူ 2022
Accepted
25 ဩ 2022
First published
31 ဩ 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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