(<i>Z</i>)-Selective anti-Markovnikov or Markovnikov thiol–yne-click reactions of an internal alkyne by amide hydrogen bond control
Milan Pramanik, Khokan Choudhuri, Subhayan Chakraborty, Arindam Ghosh, Prasenjit Mal
Abstract
Herein, we show exclusive control of stereo and regioselective thiol-yne click (TYC) reactions of internal alkynes via amide hydrogen bond control. By exploiting appropriate hydrogen bonding interactions like N-HS, N-HN and C-HO, either (Z)-selective anti-Markovnikov or Markovnikov products could be obtained for an internal alkyne, exclusively.
Topics & Concepts
Markovnikov's ruleAlkyneChemistryAmideThiolClick chemistryHydrogen bondHydrogenCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisRegioselectivityMoleculeSulfur-Based Synthesis TechniquesClick Chemistry and ApplicationsOrganic Chemistry Cycloaddition Reactions