Regioselective SN2 reactions for rapid syntheses of azido-inositols by one-pot sequence-specific nucleophilysis

Arthi Ravi; Syed Zahid Hassan; Ajithkumar N. Vanikrishna; Kana M. Sureshan

doi:10.1039/C7CC01219E

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Regioselective S_N2 reactions for rapid syntheses of azido-inositols by one-pot sequence-specific nucleophilysis†

Arthi Ravi,^a Syed Zahid Hassan,^a Ajithkumar N. Vanikrishna^a and Kana M. Sureshan

*^a

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* Corresponding authors

^a School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, CET Campus, Thiruvananthapuram-695016, India
E-mail: kms@iisertvm.ac.in, Sureshankana@gmail.com

Abstract

Triflates of myo-inositol undergo facile solvolysis in DMSO and DMF yielding S_N2 products substituted with O-nucleophiles; DMF showed slower kinetics. Axial O-triflate undergoes faster substitution than equatorial O-triflate. By exploiting this difference in kinetics, solvent-tuning and sequence-controlled nucleophilysis, rapid synthesis of three azido-inositols of myo-configuration from myo-inositol itself has been achieved.

This article is part of the themed collection: Site-selective molecular transformations

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Article information

DOI: https://doi.org/10.1039/C7CC01219E
Article type: Communication
Submitted: 15 Feb 2017
Accepted: 10 Mar 2017
First published: 10 Mar 2017

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Chem. Commun., 2017,53, 3971-3973

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Regioselective S_N2 reactions for rapid syntheses of azido-inositols by one-pot sequence-specific nucleophilysis

A. Ravi, S. Z. Hassan, A. N. Vanikrishna and K. M. Sureshan, Chem. Commun., 2017, 53, 3971 DOI: 10.1039/C7CC01219E

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