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-controlled nucleophilysis, rapid synthesis of three azido-inositols of myo-configuration from myo-inositol itself has been achieved.
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, CET Campus, Thiruvananthapuram-695016, India. kms@iisertvm.ac.in Sureshankana@gmail.com.
Arthi
A
Ravi
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, CET Campus, Thiruvananthapuram-695016, India. kms@iisertvm.ac.in Sureshankana@gmail.com.
Syed Zahid
SZ
Hassan
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, CET Campus, Thiruvananthapuram-695016, India. kms@iisertvm.ac.in Sureshankana@gmail.com.
Ajithkumar N
AN
Vanikrishna
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, CET Campus, Thiruvananthapuram-695016, India. kms@iisertvm.ac.in Sureshankana@gmail.com.
Kana M
http://orcid.org/0000-0002-4005-3655
KM
Sureshan