Literature DB >> 18549207

Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Haifeng Du1, Baoguo Zhao, Yian Shi.   

Abstract

This paper describes a catalytic asymmetric diamination process for terminal olefins at allylic and homoallylic carbons via formal C-H activation using di-tert-butyldiaziridinone as nitrogen source with a catalyst generated from Pd2(dba)3 and chiral phosphorus amidite ligand. A wide variety of readily available terminal olefins can be effectively diaminated in good yields with high regio-, diastereo-, and enantioselectivities.

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Year:  2008        PMID: 18549207      PMCID: PMC2776772          DOI: 10.1021/ja8027394

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


  17 in total

1.  Recent advances in catalytic intramolecular C-H aminations.

Authors:  Huw M L Davies; Matthew S Long
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-06       Impact factor: 15.336

2.  Exploring the nickel-catalyzed oxidation of alkenes: a diamination by sulfamide transfer.

Authors:  Kilian Muñiz; Jan Streuff; Claas H Hövelmann; Ana Núñez
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Copper(II) acetate promoted intramolecular diamination of unactivated olefins.

Authors:  Thomas P Zabawa; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

4.  A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

5.  Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes.

Authors:  Grégory L J Bar; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

6.  Palladium(II)-catalyzed intramolecular diamination of unfunctionalized alkenes.

Authors:  Jan Streuff; Claas H Hövelmann; Martin Nieger; Kilian Muñiz
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

7.  Advancing palladium-catalyzed C-N bond formation: bisindoline construction from successive amide transfer to internal alkenes.

Authors:  Kilian Muñiz
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

8.  Chiral N-heterocyclic carbene--Pd(0)-catalyzed asymmetric diamination of conjugated dienes and triene.

Authors:  Liang Xu; Yian Shi
Journal:  J Org Chem       Date:  2007-12-21       Impact factor: 4.354

Review 9.  Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors:  S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2006-02       Impact factor: 2.817

10.  A mild Cu(I)-catalyzed regioselective diamination of conjugated dienes.

Authors:  Weicheng Yuan; Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  Org Lett       Date:  2007-05-31       Impact factor: 6.005

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  45 in total

1.  Complementary regioselectivity in the Cu(I)-catalyzed diamination of conjugated dienes to form cyclic sulfamides.

Authors:  Richard G Cornwall; Baoguo Zhao; Yian Shi
Journal:  Org Lett       Date:  2010-12-30       Impact factor: 6.005

2.  A palladium-catalyzed dehydrogenative diamination of terminal olefins.

Authors:  Bin Wang; Haifeng Du; Yian Shi
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Copper-promoted and copper-catalyzed intermolecular alkene diamination.

Authors:  Fatima C Sequeira; Benjamin W Turnpenny; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-23       Impact factor: 15.336

4.  Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Authors:  Erik W Werner; Kaveri B Urkalan; Matthew S Sigman
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

5.  An effective C-C double bond formation via Cu(I)-catalyzed dehydrogenation.

Authors:  Thomas A Ramirez; Baoguo Zhao; Yian Shi
Journal:  Tetrahedron Lett       Date:  2010-04-07       Impact factor: 2.415

6.  Synthesis of (+)-CP-99,994 via Pd(0)-catalyzed asymmetric allylic and homoallylic C-H Diamination of terminal olefin.

Authors:  Renzhong Fu; Baoguo Zhao; Yian Shi
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

7.  Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines.

Authors:  Benjamin W Turnpenny; Sherry R Chemler
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

8.  Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

Authors:  Ly Dieu Tran; James Roane; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-24       Impact factor: 15.336

9.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

10.  Cu(I)-catalyzed asymmetric diamination of conjugated dienes.

Authors:  Haifeng Du; Baoguo Zhao; Weicheng Yuan; Yian Shi
Journal:  Org Lett       Date:  2008-09-03       Impact factor: 6.005

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