Literature DB >> 19193003

Pi-nucleophile traps for metallonitrene/alkyne cascade reactions: a versatile process for the synthesis of alpha-aminocyclopropanes and beta-aminostyrenes.

Aaron R Thornton1, Véronique I Martin, Simon B Blakey.   

Abstract

The reaction of a sulfamate ester derived rhodium nitrenoid species with an alkyne produces a versatile intermediate, capable of cascading into a wide variety of secondary transformations. The nature of the intermediate has been probed by reactivity studies, and the synthetic utility of the cascade process, which facilitates the construction of complex heterocyclic structures from remarkably simple acyclic precursors, is highlighted.

Entities:  

Year:  2009        PMID: 19193003     DOI: 10.1021/ja809078d

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


  10 in total

1.  Chemoselective amination of propargylic C(sp³)-H bonds by cobalt(II)-based metalloradical catalysis.

Authors:  Hongjian Lu; Chaoqun Li; Huiling Jiang; Christopher L Lizardi; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

2.  Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction.

Authors:  Nels C Gerstner; Christopher S Adams; Maik Tretbar; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

3.  Synthesis and biological evaluation of 2',4'- and 3',4'-bridged nucleoside analogues.

Authors:  K C Nicolaou; Shelby P Ellery; Fatima Rivas; Karen Saye; Eric Rogers; Tyler J Workinger; Mark Schallenberger; Rommel Tawatao; Ana Montero; Ann Hessell; Floyd Romesberg; Dennis Carson; Dennis Burton
Journal:  Bioorg Med Chem       Date:  2011-07-23       Impact factor: 3.641

4.  Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

Authors:  Quyen Nguyen; Tuyen Nguyen; Tom G Driver
Journal:  J Am Chem Soc       Date:  2013-01-03       Impact factor: 15.419

5.  Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.

Authors:  Josephine Eshon; Nels C Gerstner; Jennifer M Schomaker
Journal:  ARKIVOC       Date:  2018-11-26       Impact factor: 1.140

6.  Rhodium-catalyzed synthesis of 2,3-disubstituted indoles from β,β-disubstituted stryryl azides.

Authors:  Ke Sun; Sheng Liu; Patryk M Bec; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-14       Impact factor: 15.336

7.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

8.  Intramolecular 1,5-C(sp3)-H Radical Amination via Co(II)-Based Metalloradical Catalysis for Five-Membered Cyclic Sulfamides.

Authors:  Hongjian Lu; Kai Lang; Huiling Jiang; Lukasz Wojtas; X Peter Zhang
Journal:  Chem Sci       Date:  2016-07-28       Impact factor: 9.825

9.  Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C-H bond insertion cascades.

Authors:  Jiun-Le Shih; Santa Jansone-Popova; Christopher Huynh; Jeremy A May
Journal:  Chem Sci       Date:  2017-09-04       Impact factor: 9.825

10.  Rh2(II)-catalyzed selective aminomethylene migration from styryl azides.

Authors:  Chen Kong; Navendu Jana; Tom G Driver
Journal:  Org Lett       Date:  2013-02-04       Impact factor: 6.005

  10 in total

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