An access to highly enantioenriched cis-3,5-disubstituted γ-lactones from α-bromoacetate and silyl enol ether?

Organic & Biomolecular Chemistry Pub Date: 2021-08-20 DOI: 10.1039/D1OB01403J

Abstract

A novel synthetic strategy for highly enantioenriched cis-3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of this synthetic method was further demonstrated through the concise stereodivergent synthesis of cis- and trans-2,4-disubstituted tetrahydrofurans.

Graphical abstract: An access to highly enantioenriched cis-3,5-disubstituted γ-lactones from α-bromoacetate and silyl enol ether
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