An Improved Stereocontrolled Access Route to Piperidine or Azepane β‐Amino Esters and Azabicyclic β‐ and γ‐Lactams; Synthesis of Novel Functionalized Azaheterocyles
Lamiaa Ouchakour, Melinda Nonn, Attila Márió Remete, Lóránd Kiss
Abstract
Abstract An improved, efficient synthesis of some functionalized saturated azaheterocycles has been accomplished by controlled functionalization of various readily available cyclic compounds containing ring C=C bond. The stereocontrolled synthetic concept was based on the oxidative ring cleavage of various unsaturated scaffolds across ozonolysis followed by ring closing with double reductive amination with primary alkylamines or fluorinated alkylamines. The protocol provided versatile azaheterocyclic derivatives with a piperidine or azepane framework.
Topics & Concepts
ChemistryPiperidineOzonolysisReductive aminationRing (chemistry)AminationCombinatorial chemistryBond cleavageStereochemistryOrganic chemistryCatalysisFluorine in Organic ChemistrySynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms