Work

Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement

Year: 2022

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.1c02804

Authors: Jeewani P. Ariyarathna, Nur-E Alom, Leo P. Roberts, Navdeep Kaur, Fan Wu, Wei Li

Institution: University of Toledo

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Halogenase Inspired Chemical Catalysis and Methods