Lewis Acid Catalyzed Ring-Opening 1,3-Aminothiolation of Donor–Acceptor Cyclopropanes Using Sulfenamides
Avishek Guin, Thukaram Rathod, Rahul N. Gaykar, Tony Roy, Akkattu T. Biju
Abstract
catalyzed mild and regioselective ring-opening 1,3-aminothiolation of donor-acceptor (D-A) cyclopropanes using sulfenamides has been demonstrated. The insertion of the C-C σ-bond of D-A cyclopropanes into the S-N σ-bond of sulfenamides allows the synthesis of diverse γ-aminated α-thiolated malonic diesters in moderate to good yields (up to 87%) with good functional group compatibility. The stereospecificity of the reaction was demonstrated using enantiomerically pure D-A cyclopropane.
Topics & Concepts
ChemistryCyclopropaneRegioselectivityRing (chemistry)CatalysisLewis acids and basesAcceptorStereospecificityMedicinal chemistryOrganic chemistryPhysicsCondensed matter physicsCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesCatalytic Alkyne Reactions