Literature DB >> 22888177

Methods for direct alkene diamination, new & old.

Sam de Jong1, Daniel G Nosal, Duncan J Wardrop.   

Abstract

The 1,2-diamine moiety is a ubiquitous structural motif present in a wealth of natural products, including non-proteinogenic amino acids and numerous alkaloids, as well as in pharmaceutical agents, chiral ligands and organic reagents. The biological activity associated with many of these systems and their chemical utility in general has ensured that the development of methods for their preparation is of critical importance. While a wide range of strategies for the preparation of 1,2-diamines have been established, the diamination of alkenes offers a particularly direct and efficient means of accessing these systems. The purpose of this review is to provide an overview of all methods of direct alkene diamination, metal-mediated or otherwise.

Entities:  

Year:  2012        PMID: 22888177      PMCID: PMC3413304          DOI: 10.1016/j.tet.2012.03.036

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  188 in total

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Journal:  Chem Rev       Date:  1999-09-08       Impact factor: 60.622

4.  trans-1,2-Diaminocyclohexane Derivatives as Chiral Reagents, Scaffolds, and Ligands for Catalysis: Applications in Asymmetric Synthesis and Molecular Recognition.

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Journal:  Chem Rev       Date:  1997-12-18       Impact factor: 60.622

5.  Modular Peptide Synthetases Involved in Nonribosomal Peptide Synthesis.

Authors:  Mohamed A. Marahiel; Torsten Stachelhaus; Henning D. Mootz
Journal:  Chem Rev       Date:  1997-11-10       Impact factor: 60.622

Review 6.  Marine natural products.

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Journal:  Nat Prod Rep       Date:  2002-02       Impact factor: 13.423

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Authors:  Jack D Scott; Robert M Williams
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

8.  Stable Polymer-Bound Iodine Azide.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-09       Impact factor: 15.336

9.  Introduction of heteroatom-based substituents into 1,4-dihydropyridines by means of a halogen-mediated, oxidative protocol: diamination, sulfonylation, sulfinylation, bis-sulfanylation, and halo-phosphonylation processes

Authors: 
Journal:  Chemistry       Date:  2000-05-15       Impact factor: 5.236

10.  Studies on the formation and incorporation of streptolidine in the biosynthesis of the peptidyl nucleoside antibiotic streptothricin F.

Authors:  Michael D Jackson; Steven J Gould; T Mark Zabriskie
Journal:  J Org Chem       Date:  2002-05-03       Impact factor: 4.354

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  20 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.  Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination.

Authors:  Shuklendu D Karyakarte; Fatima C Sequeira; Garrick H Zibreg; Guoqing Huang; Josiah P Matthew; Marina M M Ferreira; Sherry R Chemler
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  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

4.  Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.

Authors:  Sherry R Chemler; Shuklendu D Karyakarte; Zainab M Khoder
Journal:  J Org Chem       Date:  2017-09-29       Impact factor: 4.354

5.  Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.

Authors:  Kun Shen; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-09-05       Impact factor: 15.419

6.  2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Authors:  Steven J Malcolmson; Kangnan Li; Xinxin Shao
Journal:  Synlett       Date:  2019-03-26       Impact factor: 2.454

7.  Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.

Authors:  Zainab M Khoder; Christina E Wong; Sherry R Chemler
Journal:  ACS Catal       Date:  2017-06-15       Impact factor: 13.084

8.  Are homoleptic complexes of ethylene with group 12 metals isolable in solution? A DFT study.

Authors:  Mauro Fianchini; Nuno A G Bandeira
Journal:  J Mol Model       Date:  2018-06-14       Impact factor: 1.810

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.  Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Brady T Worrell; Nicklas Selander; Rakesh K Sit; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

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