Literature DB >> 12945888

The tethered aminohydroxylation (TA) reaction.

Timothy J Donohoe1, Peter D Johnson, Richard J Pye.   

Abstract

Since Sharpless' discovery of the asymmetric aminohydroxylation (AA) reaction, a major challenge for chemists has been to find ways of controlling the regio- and stereochemical outcome of this important reaction. Detailed herein is a review of our novel approach towards gaining reliable and predictable regio- and stereocontrol through the use of a tethered carbamate to promote an intramolecular AA reaction, along with a description of the mechanism proposed for this new methodology.

Entities:  

Year:  2003        PMID: 12945888     DOI: 10.1039/b305189g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  6 in total

1.  Syntheses of carbocyclic aminonucleosides and (-)-epi-4'-carbocyclic puromycin: Application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations.

Authors:  Cara Cesario; Lawrence P Tardibono; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-06-09       Impact factor: 2.415

2.  Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions.

Authors:  Christopher L Carroll; A Richard Chamberlin
Journal:  Tetrahedron Lett       Date:  2011-08-03       Impact factor: 2.415

3.  Synthesis of new (-)-bestatin-based inhibitor libraries reveals a novel binding mode in the S1 pocket of the essential malaria M1 metalloaminopeptidase.

Authors:  Geetha Velmourougane; Michael B Harbut; Seema Dalal; Sheena McGowan; Christine A Oellig; Nataline Meinhardt; James C Whisstock; Michael Klemba; Doron C Greenbaum
Journal:  J Med Chem       Date:  2011-03-02       Impact factor: 7.446

4.  Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide.

Authors:  Hao Li; Ross A Widenhoefer
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

5.  Synthesis of the dysiherbaine tetrahydropyran core employing a tethered aminohydroxylation reaction.

Authors:  Jamie L Cohen; A Richard Chamberlin
Journal:  Tetrahedron Lett       Date:  2007-04-02       Impact factor: 2.415

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

  6 in total

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