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Predicting Catalyst Extrudate Breakage Based on the Modulus of Rupture
Published on: May 13, 2018
Synthesis of α-alkylated γ-butyrolactones with concomitant anhydride kinetic resolution using a sulfamide-based
Romain Claveau1, Brendan Twamley1, Stephen J Connon1
1School of Chemistry Trinity Biomedical Sciences Institute, Trinity College Dublin 152-160, Pearse Street, Dublin 2, Ireland. connons@tcd.ie.
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.
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