Literature DB >> 16492017

N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation reaction.

Timothy J Donohoe1, Majid J Chughtai, David J Klauber, David Griffin, Andrew D Campbell.   

Abstract

The use of N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation (TA) reaction is reported. These new conditions obviate the requirement for lithium hydroxide and tBuOCl in the oxidation mixture. In addition to providing aminohydroxylation products in good yields, the catalyst loadings can be reduced to just 1 mol % osmium. Moreover, for the first time, homoallylic alcohols are now viable substrates for the TA reaction.

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Year:  2006        PMID： 16492017     DOI： 10.1021/ja057389g

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


  10 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.  Dihydropyranone formation by ipso C-H activation in a glucal 3-carbamate-derived rhodium acyl nitrenoid.

Authors:  Brisa Hurlocker; Nadia C Abascal; Lindsay M Repka; Elsy Santizo-Deleon; Abigail L Smenton; Victoria Baranov; Ritu Gupta; Sarah E Bernard; Shenjuti Chowdhury; Christian M Rojas
Journal:  J Org Chem       Date:  2011-03-07       Impact factor: 4.354

4.  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

5.  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.  Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.

Authors:  Peter H Fuller; Jin-Woo Kim; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

7.  Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism.

Authors:  Eric S Sherman; Peter H Fuller; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Org Chem       Date:  2007-04-12       Impact factor: 4.354

8.  Diastereoselective pyrrolidine synthesis via copper promoted intramolecular aminooxygenation of alkenes: formal synthesis of (+)-monomorine.

Authors:  Monissa C Paderes; Sherry R Chemler
Journal:  Org Lett       Date:  2009-05-07       Impact factor: 6.005

Review 9.  In situ tether formation from amines and alcohols enabling highly selective Tsuji-Trost allylation and olefin functionalization.

Authors:  Ugo Orcel; Jérôme Waser
Journal:  Chem Sci       Date:  2016-11-10       Impact factor: 9.825

10.  Tethered aminohydroxylation: synthesis of the β-amino acid of microsclerodermins A and B.

Authors:  Robert D C Pullin; Akshat H Rathi; Ekaterina Y Melikhova; Christian Winter; Amber L Thompson; Timothy J Donohoe
Journal:  Org Lett       Date:  2013-10-16       Impact factor: 6.005
  10 in total

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