Literature DB >> 27778502

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

Artur K Mailyan1, Kyle Young1, Joanna L Chen1, Bradley T Reid1, Armen Zakarian1.   

Abstract

A method for a directed stereoselective guanidinylation of alkenes is described. The guanidine unit can be delivered as an intact fragment by a hydroxy or carboxy group, usually with a high level of stereocontrol. After the guanidine delivery, the directing group can be cleaved under exceptionally mild conditions, typically by alcoholysis in the presence of acetic acid. Broad functional group tolerance and mild reaction conditions for the cycloguanidilation suggest applications in medicinal chemistry and natural products synthesis.

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Year:  2016        PMID： 27778502      PMCID： PMC5598158          DOI： 10.1021/acs.orglett.6b02778

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


  39 in total

1.  Diamination of conjugated dienes and trienes catalyzed by N-heterocyclic carbene-pd(0) complexes.

Authors:  Liang Xu; Haifeng Du; Yian Shi
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

2.  A Pd(0)-catalyzed diamination of terminal olefins at allylic and homoallylic carbons via formal C-H activation under solvent-free conditions.

Authors:  Haifeng Du; Weicheng Yuan; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2007-05-24       Impact factor: 15.419

3.  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

4.  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

5.  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

6.  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

7.  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

8.  (+)-saxitoxin: a first and second generation stereoselective synthesis.

Authors:  James J Fleming; Matthew D McReynolds; J Du Bois
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

9.  Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: improved reaction conditions and expanded substrate scope.

Authors:  Thomas P Zabawa; Sherry R Chemler
Journal:  Org Lett       Date:  2007-04-21       Impact factor: 6.005

10.  Oxidative diamination of alkenes with ureas as nitrogen sources: mechanistic pathways in the presence of a high oxidation state palladium catalyst.

Authors:  Kilian Muñiz; Claas H Hövelmann; Jan Streuff
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419
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  5 in total

1.  Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation.

Authors:  Bradley T Reid; Artur K Mailyan; Armen Zakarian
Journal:  J Org Chem       Date:  2018-06-22       Impact factor: 4.354

2.  Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.

Authors:  V Raghavendra Rao Kovvuri; Haoran Xue; Daniel Romo
Journal:  Org Lett       Date:  2020-02-03       Impact factor: 6.005

3.  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

4.  Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  Luke J Peterson; Jingyi Luo; John P Wolfe
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

5.  Gram-scale total synthesis of teixobactin promoting binding mode study and discovery of more potent antibiotics.

Authors:  Yu Zong; Fang Fang; Kirsten J Meyer; Liguo Wang; Zhihao Ni; Hongying Gao; Kim Lewis; Jingren Zhang; Yu Rao
Journal:  Nat Commun       Date:  2019-07-22       Impact factor: 14.919
  5 in total

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