Cyclopropanation of Propargyl Sulfonium Salts: Highly Diastereoselective Synthesis of Alkynylcyclopropanes
Yiming Zhou, You Huang
Abstract
The first propargyl sulfur ylides involving a cyclopropanation reaction between propargyl sulfonium salts and acrylonitrile derivatives is presented. Propargyl sulfonium salts act as unusual alkyne-group-delivering reagents in this transformation. Various alkynylcyclopropanes bearing three contiguous stereocenters were constructed in moderate to high yields with excellent diastereoselectivity under mild reaction conditions.
Topics & Concepts
SulfoniumPropargylCyclopropanationChemistryStereocenterAcrylonitrileReagentOrganic chemistryMedicinal chemistrySalt (chemistry)CatalysisEnantioselective synthesisPolymerCopolymerCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesCatalytic Alkyne Reactions