Literature DB >> 20945857

Metalated aziridines for cross-coupling with aryl and alkenyl halides via palladium catalysis.

John M Nelson1, Edwin Vedejs.   

Abstract

The palladium-catalyzed coupling of an aziridinylzinc chloride intermediate with alkenyl and aryl halides has been demonstrated. The method provides products with retention of aziridine stereochemistry. The utility of the coupling procedure is illustrated in the synthesis of structures related to l-furanomycin.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20945857      PMCID： PMC2996137          DOI： 10.1021/ol101904a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

Review 1.  Aziridinyl anions: generation, reactivity, and use in modern synthetic chemistry.

Authors:  Saverio Florio; Renzo Luisi
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  Substituted aziridines by lithiation-electrophile trapping of terminal aziridines.

Authors:  David M Hodgson; Philip G Humphreys; John G Ward
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

3.  Preparation of functionalized, conformationally constrained DTPA analogues from L- or D-serine and trans-4-hydroxy-L-proline. Hydroxymethyl substituents on the central acetic acid and on the backbone.

Authors:  I F Pickersgill; H Rapoport
Journal:  J Org Chem       Date:  2000-06-30       Impact factor: 4.354

4.  A General Approach to L-(+)-Furanomycin and Some Stereoisomers and Analogues Using Furoisoxazoline Intermediates Syntheses via Isoxazolines, Part 24. Part of the planned dissertation of P. J. Zimmermann. We thank the Volkswagen-Stiftung, Hannover, the Fonds der Chemischen Industrie, the Landesgraduiertenförderung Baden-Württemberg (doctoral fellowship to P.J.Z.), and Bayer AG, Wuppertal, for financial support of this work. I.B. gratefully acknowledges a grant from the Volkswagen-Stiftung for a research stay at Stuttgart. We thank Dr. W. Frey for the X-ray crystal structure determinations. This work was presented at the 17th ICHC, Vienna, in August 1999, Book of Abstracts OP-61. Part 23: ref. 1.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-03       Impact factor: 15.336

5.  Regio- and stereoselective lithiation of 2,3-diphenylaziridines: a multinuclear NMR investigation.

Authors:  Vito Capriati; Saverio Florio; Renzo Luisi; Andrea Mazzanti; Biagia Musio
Journal:  J Org Chem       Date:  2008-03-22       Impact factor: 4.354

6.  Synthesis of N-allylideneamines and their use for the double nucleophilic addition of ketene silyl (thio)acetals and trimethylsilyl cyanide.

Authors:  Isao Mizota; Yuri Matsuda; Iwao Hachiya; Makoto Shimizu
Journal:  Org Lett       Date:  2008-08-15       Impact factor: 6.005

7.  Dimerization and isomerization reactions of alpha-lithiated terminal aziridines.

Authors:  David M Hodgson; Philip G Humphreys; Steven M Miles; Christopher A J Brierley; John G Ward
Journal:  J Org Chem       Date:  2007-11-17       Impact factor: 4.354

8.  Serine-cis-proline and serine-trans-proline isosteres: stereoselective synthesis of (Z)- and (E)-alkene mimics by Still-Wittig and Ireland-Claisen rearrangements.

Authors:  Xiaodong J Wang; Scott A Hart; Bailing Xu; Matthew D Mason; John R Goodell; Felicia A Etzkorn
Journal:  J Org Chem       Date:  2003-03-21       Impact factor: 4.354
  8 in total
  2 in total

1.  Synthesis and purification of iodoaziridines involving quantitative selection of the optimal stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; James A Bull
Journal:  J Vis Exp       Date:  2014-05-16       Impact factor: 1.355

2.  Synthesis of cis-C-iodo-N-tosyl-aziridines using diiodomethyllithium: reaction optimization, product scope and stability, and a protocol for selection of stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; Aaron D Trowbridge; James A Bull
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.