Unique Reactivity of α‐Substituted Electron‐Deficient Allenes using Sulfinate Salts as Lewis Base Organocatalysts

Thomas Martzel, Jean‐François Lohier, Annie−Claude Gaumont, Jean‐François Brière, Stéphane Perrio

Advanced Synthesis & Catalysis · 2016 · 20 citations · 43 references

Concepts

Abstract

Abstract The efficient sulfinate‐catalyzed intermolecular addition reaction of α‐substituted allenyl sulfones and allenoates with Michael acceptors is highlighted. The sequence proceeds under mild conditions to provide a scalable and efficient access to versatile functionalized alkynes, displaying a quaternary stereocentre at the propargylic position. This work enriches the diversity of Lewis base organocatalysts in the field of allene chemistry, in addition to the well‐established phosphine and amine catalysts. magnified image

References

43