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. 2021 Dec 1;19(46):10201-10209.
doi: 10.1039/d1ob01921j.

Stereoselective sulfenylation of oxindole-derived propargyl alcohols to access sulfenylated-3-alkenyloxindoles

Tabassum Khan  1 , Pallava Rajesh  1 , Doma Arun  1 , Srinivasarao Yaragorla  1
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Stereoselective sulfenylation of oxindole-derived propargyl alcohols to access sulfenylated-3-alkenyloxindoles

Tabassum Khan et al. Org Biomol Chem. .

Abstract

A Ca-catalyzed, tetrasubstituted alkenyl-sulfenylation was achieved using readily available aryl/alkyl thiols and easily prepared oxindole-derived propargyl alcohols under solvent-free conditions. The reaction proceeded with hydrogen bonding assisted regioselective α-thiolation and subsequent calcium catalyzed stereoselective alkenylation to yield E-alkenyl thioethers with high diastereoselectivity.

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