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

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

Triflates of myo-inositol undergo facile solvolysis in DMSO and DMF yielding SN2 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-con...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2017-04, Vol.53 (28), p.3971-3973
Hauptverfasser: Ravi, Arthi, Hassan, Syed Zahid, Vanikrishna, Ajithkumar N, Sureshan, Kana M
Format: Artikel
Sprache:eng
Schlagworte:
Reaction kinetics
Solvolysis
Synthesis
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Zusammenfassung:Triflates of myo-inositol undergo facile solvolysis in DMSO and DMF yielding SN2 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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc01219e