Literature DB >> 21378869

Metal-catalysed 1,2-diamination reactions.

Francesca Cardona1, Andrea Goti.   

Abstract

The 1,2-diamine motif is present in a number of natural products with interesting biological activity and in many important pharmaceutical agents. Chiral 1,2-diamines are also widely used as the control elements in asymmetric synthesis and catalysis. Such compounds are thus an attractive target for the synthetic chemist. Although the diamination of an alkene seems an obvious route to these structures, far less research has been devoted to it than to the analogous dihydroxylation or aminohydroxylation reactions that are well-established processes in asymmetric synthesis. Here, we examine recent advances in metal-catalysed diamination reactions and their asymmetric variants. Given the prevalence of these structures, it seems likely that they will find extensive application in the construction of natural products and drug molecules in the near future.

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Year:  2009        PMID: 21378869     DOI: 10.1038/nchem.256

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  36 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

Review 4.  Understanding and exploiting C-H bond activation.

Authors:  Jay A Labinger; John E Bercaw
Journal:  Nature       Date:  2002-05-30       Impact factor: 49.962

5.  C-H bond functionalization in complex organic synthesis.

Authors:  Kamil Godula; Dalibor Sames
Journal:  Science       Date:  2006-04-07       Impact factor: 47.728

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

7.  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 8.  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

9.  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

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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  39 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.  1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.

Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

3.  Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.

Authors:  Ranjan Jana; Tejas P Pathak; Katrina H Jensen; Matthew S Sigman
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

4.  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

5.  Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines.

Authors:  David E Olson; Autumn Maruniak; Sushant Malhotra; Barry M Trost; J Du Bois
Journal:  Org Lett       Date:  2011-05-27       Impact factor: 6.005

6.  Regiodivergent Iridium(III)-Catalyzed Diamination of Alkenyl Amides with Secondary Amines: Complementary Access to γ- or δ-Lactams.

Authors:  John H Conway; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2017-12-26       Impact factor: 15.419

7.  Rhodium(III)-Catalyzed Three-Component 1,2-Diamination of Unactivated Terminal Alkenes.

Authors:  Sumin Lee; Young Jin Jang; Erik J T Phipps; Honghui Lei; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2020       Impact factor: 3.157

8.  Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

Authors:  Katrina H Jensen; Tejas P Pathak; Yang Zhang; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

9.  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

10.  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

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