Literature DB >> 28642627

Allenyl esters as quenching agents for ruthenium olefin metathesis catalysts.

Animesh Roy1, Maximilian A Silvestri1, Robert A Hall1, Salvatore D Lepore1.   

Abstract

In the attempt to synthesize substituted allenyl esters through a metathesis coupling of unsubstituted allenyl esters and alkenes using a variety of ruthenium catalysts, it was discovered that allenyl esters themselves cleanly arrested the activity of the catalysts. Further studies suggests possible utility of allene esters as general quenching agents for metathesis reactions. To explore this idea, several representative olefin metathesis reactions, including ring closing, were successfully terminated by the addition of simple allenyl esters for more convenient purification.

Entities:  

Keywords:  Allenyl esters; Metathesis poison; Metathesis quenching

Year:  2016        PMID: 28642627      PMCID: PMC5475365          DOI: 10.1016/j.tetlet.2016.11.121

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  13 in total

1.  Organo-manganese η2-auxiliary directed reactions: a diastereoselective approach to 2,3-allenols.

Authors:  Animesh Roy; Bilal A Bhat; Salvatore D Lepore
Journal:  Org Lett       Date:  2015-02-09       Impact factor: 6.005

2.  Asymmetric Protonation of Cumulenolates: Synthesis of Allenyl Aldehydes Facilitated by an Organomanganese Auxiliary.

Authors:  Animesh Roy; Bilal A Bhat; Salvatore D Lepore
Journal:  Org Lett       Date:  2016-02-29       Impact factor: 6.005

3.  Catalytic living ring-opening metathesis polymerization.

Authors:  Amit A Nagarkar; Andreas F M Kilbinger
Journal:  Nat Chem       Date:  2015-08-10       Impact factor: 24.427

4.  Michael-Stork addition of cyclopentyl enamine to allenyl ketones and esters.

Authors:  Maximilian A Silvestri; Deborah C Bromfield; Salvatore D Lepore
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

5.  On the mechanism of the initiation reaction in Grubbs-Hoveyda complexes.

Authors:  Vasco Thiel; Marina Hendann; Klaus-Jürgen Wannowius; Herbert Plenio
Journal:  J Am Chem Soc       Date:  2011-12-21       Impact factor: 15.419

6.  Recent mechanistic and synthetic developments in the chemistry of transition-metal vinylidene complexes.

Authors:  Jason M Lynam
Journal:  Chemistry       Date:  2010-07-26       Impact factor: 5.236

7.  Well-defined silica-supported olefin metathesis catalysts.

Authors:  Daryl P Allen; Matthew M Van Wingerden; Robert H Grubbs
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

8.  Anion-catalyzed addition of gamma-silylallenyl esters to aldehydes: a new entry into [3.2.1] bicyclic natural products.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

9.  Olefin cross-metathesis reactions at room temperature using the nonionic amphiphile "PTS": just add water.

Authors:  Bruce H Lipshutz; Grant T Aguinaldo; Subir Ghorai; Karl Voigtritter
Journal:  Org Lett       Date:  2008-03-12       Impact factor: 6.005

Review 10.  Sustainable concepts in olefin metathesis.

Authors:  Hervé Clavier; Karol Grela; Andreas Kirschning; Marc Mauduit; Steven P Nolan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

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