Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement
Jeewani P. Ariyarathna, Nur‐E Alom, Leo P. Roberts, Navdeep Kaur, Fan Wu, Wei Li
Abstract
We disclose here practical strategies toward the synthesis of morpholines and Claisen rearrangement products based on the divergent reactivity of a common halonium intermediate. These reactions employ widely available alkenes in a Lewis acid-catalyzed halo-etherification process that can then transform them into the desired products with exceptional regioselectivity for both activated and unactivated olefins. Our mechanistic probe reveals an interesting regiochemical kinetic resolution process.
Topics & Concepts
Claisen rearrangementRegioselectivityLewis acids and basesMorpholineChemistryCatalysisCarroll rearrangementCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions