Issue 43, 2020

Sulfoxonium ylides: simple compounds with chameleonic reactivity

Abstract

Sulfur ylides first disclosed in 1930 started to gain more attention in the 1960s, thanks mainly to the studies by Corey and Chaykovsky on their use for the preparation of strained rings. More recently, the chemistry of these compounds has experienced important growth, in part due to the similarity of their reactivities with diazo compounds. This short review provides an overview on the great assortment of reactions of sulfoxonium ylides, outlining a comparison between the chemistry of these ylides and their congeners: sulfonium ylides and diazo compounds. Insertion reactions, cyclisation reactions and ring-opening reactions are highlighted, giving particular attention to catalytic asymmetric methodologies.

Graphical abstract: Sulfoxonium ylides: simple compounds with chameleonic reactivity

Article information

Article type
Review Article
Submitted
03 Sep 2020
Accepted
01 Oct 2020
First published
01 Oct 2020

Org. Biomol. Chem., 2020,18, 8793-8809

Sulfoxonium ylides: simple compounds with chameleonic reactivity

G. D. Bisag, S. Ruggieri, M. Fochi and L. Bernardi, Org. Biomol. Chem., 2020, 18, 8793 DOI: 10.1039/D0OB01822H

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