Issue 4, 2022

Reversal of regioselectivity in reactions of donor–acceptor cyclopropanes with electrophilic olefins

Abstract

Reactivity of donor–acceptor cyclopropanes towards nucleophiles and electrophiles is determined by the specific philicity of the carbon atoms originating from the strong polarization of the central C–C bond. Herein, we report that vitamin B12 catalysis enables the transformation of an initially electrophilic center into a nucleophilic radical that reacts with SOMOphiles. This radical-based strategy reverses the standard regioselectivity and thus complements the classical approaches.

Graphical abstract: Reversal of regioselectivity in reactions of donor–acceptor cyclopropanes with electrophilic olefins

Supplementary files

Article information

Article type
Communication
Submitted
22 Sep 2021
Accepted
22 Nov 2021
First published
22 Nov 2021

Chem. Commun., 2022,58, 509-512

Reversal of regioselectivity in reactions of donor–acceptor cyclopropanes with electrophilic olefins

J. Turkowska, J. Durka, M. Ociepa and D. Gryko, Chem. Commun., 2022, 58, 509 DOI: 10.1039/D1CC05330B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements