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

Tabassum Khan; Pallava Rajesh; Doma Arun; Srinivasarao Yaragorla

doi:10.1039/D1OB01921J

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

Tabassum Khan,^a Pallava Rajesh,^a Doma Arun^a and Srinivasarao Yaragorla

*^a

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* Corresponding authors

^a School of Chemistry, University of Hyderabad, Telangana, India
E-mail: Srinivas.yaragorla@uohyd.ac.in, ysruoh@gmail.com

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.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D1OB01921J
Article type: Paper
Submitted: 28 Sep 2021
Accepted: 11 Nov 2021
First published: 12 Nov 2021

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Org. Biomol. Chem., 2021,19, 10201-10209

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

T. Khan, P. Rajesh, D. Arun and S. Yaragorla, Org. Biomol. Chem., 2021, 19, 10201 DOI: 10.1039/D1OB01921J

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Organic & Biomolecular Chemistry

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

Abstract

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

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