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

Jeewani P. Ariyarathna | Zendy; NurE Alom | Zendy; Leo P. Roberts | Zendy; Navdeep Kaur | Zendy; Fan Wu | Zendy; Wei Li | Zendy

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

Author(s) -

Jeewani P. Ariyarathna,

NurE Alom,

Leo P. Roberts,

Navdeep Kaur,

Fan Wu,

Wei Li

Publication year - 2022

Publication title -

the 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.

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