Literature DB >> 24147839

Synthesis of cyclic guanidines via Pd-catalyzed alkene carboamination.

Blane P Zavesky1, Nicholas R Babij, Jonathan A Fritz, John P Wolfe.   

Abstract

A new approach to the synthesis of substituted 5-membered cyclic guanidines is described. Palladium-catalyzed alkene carboamination reactions between acyclic N-allyl guanidines and aryl or alkenyl halides provide these products in good yield. This method allows access to a number of different cyclic guanidine derivatives in only two steps from readily available allylic amines.

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Year:  2013        PMID： 24147839      PMCID： PMC3857308          DOI： 10.1021/ol402377y

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


  28 in total

Review 1.  The chemistry and biology of organic guanidine derivatives.

Authors:  Roberto G S Berlinck; Antonio Carlos B Burtoloso; Amaro E Trindade-Silva; Stelamar Romminger; Raquel P Morais; Karin Bandeira; Carolina M Mizuno
Journal:  Nat Prod Rep       Date:  2010-10-18       Impact factor: 13.423

2.  Parallel synthesis of chiral pentaamines and pyrrolidine containing bis-heterocyclic libraries. Multiple scaffolds with multiple building blocks: a double diversity for the identification of new antitubercular compounds.

Authors:  Adel Nefzi; Jon Appel; Sergey Arutyunyan; Richard A Houghten
Journal:  Bioorg Med Chem Lett       Date:  2009-07-09       Impact factor: 2.823

Review 3.  The chemistry and biology of organic guanidine derivatives.

Authors:  Roberto G S Berlinck; Amaro E Trindade-Silva; Mario F C Santos
Journal:  Nat Prod Rep       Date:  2012-09-20       Impact factor: 13.423

4.  Pyrrolidine bis-cyclic guanidines with antimicrobial activity against drug-resistant Gram-positive pathogens identified from a mixture-based combinatorial library.

Authors:  Mary E Hensler; Gregory Bernstein; Victor Nizet; Adel Nefzi
Journal:  Bioorg Med Chem Lett       Date:  2006-08-04       Impact factor: 2.823

5.  Asymmetric total synthesis of (+)-merobatzelladine B.

Authors:  Nicholas R Babij; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-16       Impact factor: 15.336

6.  Room temperature ring-opening cyclization reactions of 2-vinylaziridines with isocyanates, carbodiimides, and isothiocyanates catalyzed by

Authors: 
Journal:  J Org Chem       Date:  2000-09-22       Impact factor: 4.354

Review 7.  Transition metal-catalyzed N-arylations of amidines and guanidines.

Authors:  Tom R M Rauws; Bert U W Maes
Journal:  Chem Soc Rev       Date:  2012-01-05       Impact factor: 54.564

8.  Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidines.

Authors:  Duy N Mai; John P Wolfe
Journal:  J Am Chem Soc       Date:  2010-09-08       Impact factor: 15.419

9.  Synthesis of the reported structures for kealiinines B and C.

Authors:  Joseph B Gibbons; Keith M Gligorich; Bryan E Welm; Ryan E Looper
Journal:  Org Lett       Date:  2012-09-11       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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  8 in total

1.  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

2.  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

3.  Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process.

Authors:  Gang Yan; Bereket L Zekarias; Xiaoyu Li; Victor A Jaffett; Ilia A Guzei; Jennifer E Golden
Journal:  Chemistry       Date:  2020-02-06       Impact factor: 5.236

4.  Pd-Catalyzed Alkene Diamination Reactions of Nitrogen Electrophiles: Synthesis of Cyclic Guanidines and Ureas Bearing Dialkylaminomethyl Groups.

Authors:  Luke J Peterson; Janelle K Kirsch; John P Wolfe
Journal:  Org Lett       Date:  2018-06-06       Impact factor: 6.005

5.  Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.

Authors:  Derick R White; Evan C Bornowski; John P Wolfe
Journal:  Isr J Chem       Date:  2020-01-24       Impact factor: 3.333

6.  Synthesis of Cyclic Guanidines via Silver-Catalyzed Intramolecular Alkene Hydroamination Reactions of N-Allylguanidines.

Authors:  Zachary J Garlets; Mattia Silvi; John P Wolfe
Journal:  Org Lett       Date:  2016-05-11       Impact factor: 6.005

7.  The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.

Authors:  Pavel Kočovský; Jan-E Bäckvall
Journal:  Chemistry       Date:  2014-11-05       Impact factor: 5.236

8.  Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.

Authors:  Blane P Zavesky; Nicholas R Babij; John P Wolfe
Journal:  Org Lett       Date:  2014-09-08       Impact factor: 6.005
  8 in total

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