Open AccessLewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement
Author(s) -
Jeewani Poornima Ariyarathna,
NurE Alom,
Leo P. Roberts,
Navdeep Kaur,
Fan Wu,
Wei Li
Publication year - 2022
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c02804
Subject(s) - claisen rearrangement , regioselectivity , lewis acids and bases , morpholine , chemistry , catalysis , carroll rearrangement , combinatorial chemistry , organic chemistry
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.