ArticleThe Journal of organic chemistry2022
Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.
Article in The Journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Incorporating azaheterocycle functionality in intramolecular aerobic, copper-catalyzed aminooxygenation of alkenes.RSC advances · 2024Article
- Selective C-H Activation of Unprotected Allylamines by Control of Catalyst Speciation.Chem catalysis · 2023Article
- Tunable [3+2] and [4+2] annulations for pyrrolidine and piperidine synthesis.Chemical communications (Cambridge, England) · 2023Article
- Syntheses of 2- and 3-Substituted Morpholine Congeners via Ring Opening of 2-Tosyl-1,2-Oxazetidine.The Journal of organic chemistry · 2023Article
- Reshuffle Bonds by Ball Milling: A Mechanochemical Protocol for Charge-Accelerated Aza-Claisen Rearrangements.Molecules (Basel, Switzerland) · 2023Article
Corrections and comments
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Authors and funding
6 authors.
Funding
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.
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