Copper‐Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones

Copper to the rescue: A general method for the synthesis of propargylic sulfones featuring quaternary stereocenters has been developed. The method relies on a copper‐catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates. It provides the first example of such a transition‐metal‐catalyzed enantioselective propargylic substitution reaction with sulfur‐centered nucleophiles and gives access to functionalized tertiary sulfones.

Abstract

Tertiary propargylic sulfones are of significant importance in organic synthesis and medicinal chemistry, but to date no general asymmetric synthesis approach has been developed. We disclose a versatile copper‐catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates that allows the construction of propargylic sulfones featuring elusive quaternary stereocenters. This method provides the first successful example of such an enantioselective propargylic sulfonylation, features high asymmetric induction, wide functional group tolerance, and scalability, and enables attractive product diversification.

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