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Issue 41, 2018
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Synthesis of α-alkylated γ-butyrolactones with concomitant anhydride kinetic resolution using a sulfamide-based catalyst

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Abstract

The Kinetic Resolution (KR) of α-alkylated enolisable disubstituted anhydrides has been shown to be possible for the first time. In the presence of an ad hoc designed novel class of bifunctional sulfamide organocatalyst, a regio-, diastereo- and enantioselective cycloaddition reaction between the enolisable anhydride and benzaldehydes provides densely functionalised γ-butyrolactones in one pot (up to 19 : 1 dr, 94% ee) with control over three contiguous stereocentres. The concomitant resolution of the starting material anhydride, provides access to a range of chiral succinate derivatives with selectivity factors up to S* = 10.5.

Graphical abstract: Synthesis of α-alkylated γ-butyrolactones with concomitant anhydride kinetic resolution using a sulfamide-based catalyst

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Publication details

The article was received on 11 Sep 2018, accepted on 03 Oct 2018 and first published on 11 Oct 2018


Article type: Communication
DOI: 10.1039/C8OB02248H
Citation: Org. Biomol. Chem., 2018,16, 7574-7578
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    Synthesis of α-alkylated γ-butyrolactones with concomitant anhydride kinetic resolution using a sulfamide-based catalyst

    R. Claveau, B. Twamley and S. J. Connon, Org. Biomol. Chem., 2018, 16, 7574
    DOI: 10.1039/C8OB02248H

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