Literature DB >> 12405805

The tethered aminohydroxylation (TA) of cyclic allylic carbamates.

Timothy J Donohoe1, Peter D Johnson, Andrew Cowley, Martine Keenan.   

Abstract

The tethered aminohydroxylation of cyclic allylic carbamates is described using catalytic amounts of potassium osmate. The mechanism of reaction involves formation of an imido-osmium complex which adds intramolecularly to alkenes with complete control of both regio- and stereoselectivity: the formation of syn-aminodiol motifs is now straightforward using this chemistry. Proof of the mechanism was obtained with an X-ray crystal structure of an azaglycolate osmate ester intermediate.

Entities:  

Year:  2002        PMID： 12405805     DOI： 10.1021/ja0276117

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.  Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates.

Authors:  Simran Buttar; Julia Caine; Evelyne Goné; Reneé Harris; Jennifer Gillman; Roxanne Atienza; Ritu Gupta; Kimberly M Sogi; Lauren Jain; Nadia C Abascal; Yetta Levine; Lindsay M Repka; Christian M Rojas
Journal:  J Org Chem       Date:  2018-07-06       Impact factor: 4.354

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.  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

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.  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

7.  Protecting group and solvent control of stereo- and chemoselectivity in glucal 3-carbamate amidoglycosylation.

Authors:  Ritu Gupta; Kimberly M Sogi; Sarah E Bernard; John D Decatur; Christian M Rojas
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

Review 8.  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

9.  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.  Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.

Authors:  Deng-Fu Lu; Cheng-Liang Zhu; Zhen-Xin Jia; Hao Xu
Journal:  J Am Chem Soc       Date:  2014-09-16       Impact factor: 15.419
  10 in total

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