Literature DB >> 19408926

Cu(I)-catalyzed diamination of disubstituted terminal olefins: an approach to potent NK1 antagonist.

Yuehong Wen1, Baoguo Zhao, Yian Shi.   

Abstract

This paper describes a diamination process using di-tert-butyldiaziridinone as nitrogen source and CuCl as catalyst. A wide variety of disubstituted terminal olefins can be efficiently diaminated in good yields under mild condition. This diamination process was used to synthesize potent NK(1) antagonist Sch 425078.

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Year:  2009        PMID： 19408926      PMCID： PMC2696623          DOI： 10.1021/ol900808z

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


  33 in total

1.  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

2.  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

3.  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

4.  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

5.  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

6.  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

Review 7.  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

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

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419

9.  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

10.  Cu(I)-catalyzed cycloguanidination of olefins.

Authors:  Baoguo Zhao; Haifeng Du; Yian Shi
Journal:  Org Lett       Date:  2008-02-27       Impact factor: 6.005
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  13 in total

1.  Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.

Authors:  Artur K Mailyan; Kyle Young; Joanna L Chen; Bradley T Reid; Armen Zakarian
Journal:  Org Lett       Date:  2016-10-25       Impact factor: 6.005

2.  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

Review 3.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

4.  Facile Cu(I)-catalyzed oxidative coupling of anilines to azo compounds and hydrazines with diaziridinone under mild conditions.

Authors:  Yingguang Zhu; Yian Shi
Journal:  Org Lett       Date:  2013-04-01       Impact factor: 6.005

5.  Highly efficient Cu(I)-catalyzed oxidation of alcohols to ketones and aldehydes with diaziridinone.

Authors:  Yingguang Zhu; Baoguo Zhao; Yian Shi
Journal:  Org Lett       Date:  2013-02-15       Impact factor: 6.005

6.  Cu(I)-catalyzed diamination of conjugated dienes. Complementary regioselectivity from two distinct mechanistic pathways involving Cu(II) and Cu(III) species.

Authors:  Baoguo Zhao; Xingao Peng; Yingguang Zhu; Thomas A Ramirez; Richard G Cornwall; Yian Shi
Journal:  J Am Chem Soc       Date:  2011-12-02       Impact factor: 15.419

7.  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

8.  Cu(I)-catalyzed sequential diamination and dehydrogenation of terminal olefins: a facile approach to imidazolinones.

Authors:  Yingguang Zhu; Yian Shi
Journal:  Chemistry       Date:  2014-09-11       Impact factor: 5.236

9.  A facile copper(I)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions.

Authors:  Yingguang Zhu; Yian Shi
Journal:  Org Biomol Chem       Date:  2013-11-21       Impact factor: 3.876

10.  Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)-Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures.

Authors:  Huiling Jiang; Kai Lang; Hongjian Lu; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-11       Impact factor: 15.336
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