Literature DB >> 35142512

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

Jeewani P Ariyarathna1, Nur-E Alom1, Leo P Roberts1, Navdeep Kaur1, Fan Wu1, Wei Li1.   

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.

Entities:  

Mesh：

Substances：

Year:  2022        PMID： 35142512      PMCID： PMC9205334          DOI： 10.1021/acs.joc.1c02804

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.198


  56 in total

Review 1.  Recent developments in the chemistry of polyvalent iodine compounds.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2002-07       Impact factor: 60.622

2.  Palladium-Catalyzed Carbocyclizations of Unactivated Alkyl Bromides with Alkenes Involving Auto-tandem Catalysis.

Authors:  Alexander R O Venning; Megan R Kwiatkowski; Joan E Roque Peña; Brendan C Lainhart; Akil A Guruparan; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

3.  Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

Authors:  Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2019-06-04       Impact factor: 15.419

4.  Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation.

Authors:  Fan Wu; Nur-E Alom; Jeewani P Ariyarathna; Johannes Naß; Wei Li
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-17       Impact factor: 15.336

5.  Catalytic Regio- and Stereoselective Alkene Sulfenoamination for 1,4-Benzothiazine Synthesis.

Authors:  Nur-E Alom; Navdeep Kaur; Fan Wu; Shannon Jasmine Saluga; Wei Li
Journal:  Chemistry       Date:  2019-05-02       Impact factor: 5.236

6.  One-step synthesis of saturated spirocyclic N-heterocycles with stannyl amine protocol (SnAP) reagents and ketones.

Authors:  Woon-Yew Siau; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2014-12-09       Impact factor: 15.419

7.  A telluride-triggered nucleophilic ring opening of monoactivated cyclopropanes.

Authors:  Dmitry V Avilov; Mahesh G Malusare; Engin Arslancan; Donald C Dittmer
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

8.  An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from beta-heteroatom amino compounds and vinyl sulfonium salts.

Authors:  Muhammad Yar; Eoghan M McGarrigle; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  New strategy for the synthesis of substituted morpholines.

Authors:  Matthew L Leathen; Brandon R Rosen; John P Wolfe
Journal:  J Org Chem       Date:  2009-07-17       Impact factor: 4.354

10.  Enantioselective Total Synthesis and Structural Revision of Dysiherbol A.

Authors:  Julian Baars; Isabelle Grimm; Dirk Blunk; Jörg-Martin Neudörfl; Hans-Günther Schmalz
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-01       Impact factor: 15.336
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.