Literature DB >> 21732656

Metal-free oxyaminations of alkenes using hydroxamic acids.

Valerie A Schmidt1, Erik J Alexanian.   

Abstract

A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.

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Year:  2011        PMID： 21732656     DOI： 10.1021/ja204255e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  16 in total

1.  Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  J Org Chem       Date:  2019-01-17       Impact factor: 4.354

2.  Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.

Authors:  Fatima C Sequeira; Sherry R Chemler
Journal:  Org Lett       Date:  2012-08-15       Impact factor: 6.005

3.  Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.

Authors:  Honghui Lei; John H Conway; Caleb C Cook; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-07-16       Impact factor: 15.419

4.  Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media.

Authors:  Yuanxiang Wang; Brendan Frett; Nick McConnell; Hong-Yu Li
Journal:  Org Biomol Chem       Date:  2015-03-14       Impact factor: 3.876

Review 5.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

6.  Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.

Authors:  Monissa C Paderes; Jerome B Keister; Sherry R Chemler
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

7.  Synthesis of vicinal aminoalcohols by stereoselective aza-Wacker cyclizations: access to (-)-acosamine by redox relay.

Authors:  Adam B Weinstein; David P Schuman; Zhi Xu Tan; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336

8.  Synthesis of trifluoromethylated isoxazolidines: 1,3-dipolar cycloaddition of nitrosoarenes, (trifluoromethyl)diazomethane, and alkenes.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  Org Lett       Date:  2013-06-11       Impact factor: 6.005

9.  Iron catalyzed asymmetric oxyamination of olefins.

Authors:  Kevin S Williamson; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

10.  A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core.

Authors:  Nicholas G W Cowper; Matthew J Hesse; Katie M Chan; Sarah E Reisman
Journal:  Chem Sci       Date:  2020-10-15       Impact factor: 9.825
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