953986-10-2Relevant articles and documents
Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement
Ariyarathna, Jeewani P.,Alom, Nur-E,Roberts, Leo P.,Kaur, Navdeep,Wu, Fan,Li, Wei
, p. 2947 - 2958 (2022/02/23)
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.