Issue 42, 2021

Photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters

Abstract

A mild photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters in an aqueous medium was developed. The sequential reaction process comprising the intramolecular radical addition of α-bromo-β-keto esters to olefins under photoredox catalysis, and subsequent cyclization to form cyclopropane proceeds in one-pot under exceptionally mild conditions at room temperature in the presence of 2,6-lutidine. A broad range of substrates consisting of various alkenes and both base- and acid-sensitive functionalized esters were feasible under the reaction conditions, resulting in a wide range of functionalized bicyclic cyclopropanes.

Graphical abstract: Photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters

Supplementary files

Article information

Article type
Communication
Submitted
04 Sep 2021
Accepted
02 Oct 2021
First published
09 Oct 2021

Org. Biomol. Chem., 2021,19, 9172-9176

Photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters

K. Ide, M. Furuta and H. Tokuyama, Org. Biomol. Chem., 2021, 19, 9172 DOI: 10.1039/D1OB01733K

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