Literature DB >> 19617985

Catalytic amide formation with alpha'-hydroxyenones as acylating reagents.

Pei-Chen Chiang1, Yoonjoo Kim, Jeffrey W Bode.   

Abstract

Alpha'-hydroxyenones undergo clean, catalytic amidations with amines promoted by the combination of an N-heterocyclic carbene and 1,2,4-triazole.

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Year:  2009        PMID： 19617985      PMCID： PMC2893382          DOI： 10.1039/b909360e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  25 in total

Review 1.  Emerging methods in amide- and peptide-bond formation.

Authors:  Jeffery W Bode
Journal:  Curr Opin Drug Discov Devel       Date:  2006-11

2.  Extending mechanistic routes in heterazolium catalysis--promising concepts for versatile synthetic methods.

Authors:  Kirsten Zeitler
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-25       Impact factor: 15.336

3.  N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols.

Authors:  Mohammad Movassaghi; Michael A Schmidt
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

Review 4.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

5.  Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature.

Authors:  Raed M Al-Zoubi; Olivier Marion; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Catalyzed dehydrogenative coupling of primary alcohols with water, methanol, or amines.

Authors:  Theo Zweifel; Jean-Valère Naubron; Hansjörg Grützmacher
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2007-10-11       Impact factor: 15.419

8.  N-heterocyclic carbene-catalyzed generation of homoenolates: gamma-butyrolactones by direct annulations of enals and aldehydes.

Authors:  Stephanie S Sohn; Evelyn L Rosen; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2004-11-10       Impact factor: 15.419

9.  Amide synthesis from alcohols and amines by the extrusion of dihydrogen.

Authors:  Lars Ulrik Nordstrøm; Henning Vogt; Robert Madsen
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

10.  Alpha'-hydroxy enones as achiral templates for Lewis acid-catalyzed enantioselective Diels-Alder reactions.

Authors:  Claudio Palomo; Mikel Oiarbide; Jesús M García; Alberto González; Elena Arceo
Journal:  J Am Chem Soc       Date:  2003-11-19       Impact factor: 15.419
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  12 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Asymmetric N-Heterocyclic Carbene (NHC) Catalyzed Acyl Anion Reactivity.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  Aldrichimica Acta       Date:  2011       Impact factor: 3.667

3.  Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals.

Authors:  Philip Wheeler; Harit U Vora; Tomislav Rovis
Journal:  Chem Sci       Date:  2013-04       Impact factor: 9.825

Review 4.  Rethinking amide bond synthesis.

Authors:  Vijaya R Pattabiraman; Jeffrey W Bode
Journal:  Nature       Date:  2011-12-21       Impact factor: 49.962

5.  Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

Authors:  Jessada Mahatthananchai; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  ACS Catal       Date:  2012-02-29       Impact factor: 13.084

6.  α,β-Unsaturated acyl azoliums from N-heterocyclic carbene catalyzed reactions: observation and mechanistic investigation.

Authors:  Jessada Mahatthananchai; Pinguan Zheng; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-05       Impact factor: 15.336

7.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

8.  The effect of the N-mesityl group in NHC-catalyzed reactions.

Authors:  Jessada Mahatthananchai; Jeffrey W Bode
Journal:  Chem Sci       Date:  2012-01-01       Impact factor: 9.825

9.  Bio-inspired NHC-organocatalyzed Stetter reaction in aqueous conditions.

Authors:  Mégane Debiais; Aladin Hamoud; Reihana Drain; Philippe Barthélémy; Valérie Desvergnes
Journal:  RSC Adv       Date:  2020-11-09       Impact factor: 4.036

10.  Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.

Authors:  Kenneth E Schwieter; Bo Shen; Jessica P Shackleford; Matthew W Leighty; Jeffrey N Johnston
Journal:  Org Lett       Date:  2014-09-08       Impact factor: 6.005
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