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Literature DB >> 16448117

Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes.

Christian Fischer¹, Sean W Smith, David A Powell, Gregory C Fu.

Abstract

N-Heterocyclic carbenes can catalyze beta-alkylations of a range of alpha,beta-unsaturated esters, amides, and nitriles that bear pendant leaving groups to form a variety of ring sizes. In this process, the nucleophilic catalyst transiently transforms the normally electrophilic beta carbon into a nucleophilic site through an unanticipated addition-tautomerization sequence.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2006 PMID： 16448117 PMCID： PMC2553003 DOI： 10.1021/ja058222q

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

9 in total

1. Recent advances in the Baylis-Hillman reaction and applications.

Authors: Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal: Chem Rev Date: 2003-03 Impact factor: 60.622

2. N-heterocyclic carbenes: reagents, not just ligands!

Authors: Vijay Nair; Santhamma Bindu; Vellalath Sreekumar
Journal: Angew Chem Int Ed Engl Date: 2004-10-04 Impact factor: 15.336

3. Organocatalyzed conjugate umpolung of alpha,beta-unsaturated aldehydes for the synthesis of gamma-butyrolactones.

Authors: Christian Burstein; Frank Glorius
Journal: Angew Chem Int Ed Engl Date: 2004-11-19 Impact factor: 15.336

4. 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

5. Organomediated Morita-Baylis-Hillman cyclization reactions.

Authors: Marie E Krafft; Thomas F N Haxell
Journal: J Am Chem Soc Date: 2005-07-27 Impact factor: 15.419

6. Unprecedented reactivity in the Morita-Baylis-Hillman reaction; intramolecular alpha-alkylation of enones using saturated alkyl halides.

Authors: Marie E Krafft; Kimberly A Seibert; Thomas F N Haxell; Chitaru Hirosawa
Journal: Chem Commun (Camb) Date: 2005-11-04 Impact factor: 6.222

7. 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

8. Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents.

Authors: David A Powell; Toshihide Maki; Gregory C Fu
Journal: J Am Chem Soc Date: 2005-01-19 Impact factor: 15.419

9. Nucleophilic carbenes in asymmetric organocatalysis.

Authors: Dieter Enders; Tim Balensiefer
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

9 in total

12 in total

Review 1. Carbene catalysts.

Authors: Jennifer L Moore; Tomislav Rovis
Journal: Top Curr Chem Date: 2010

Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes.

1. Recent advances in the Baylis-Hillman reaction and applications.

2. N-heterocyclic carbenes: reagents, not just ligands!

3. Organocatalyzed conjugate umpolung of alpha,beta-unsaturated aldehydes for the synthesis of gamma-butyrolactones.

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

5. Organomediated Morita-Baylis-Hillman cyclization reactions.

6. Unprecedented reactivity in the Morita-Baylis-Hillman reaction; intramolecular alpha-alkylation of enones using saturated alkyl halides.

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

8. Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents.

9. Nucleophilic carbenes in asymmetric organocatalysis.

Review 1. Carbene catalysts.

Review 2. Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

3. N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones.

4. N-Heterocyclic Carbene-Promoted Rauhut]Currier Reactions between Vinyl Sulfones and α,β-Unsaturated Aldehydes.

5. N-heterocyclic carbene-catalyzed conjugate additions of alcohols.

6. 5-Benzyl-2-phenyl-6,8-dihydro-5H-1,2,4-triazolo[3,4-c][1,4]oxazin-2-ium hexa-fluoridophosphate.

7. S_NAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.

8. 2,5-Diphenyl-2,5,6,8-tetra-hydro-1,2,4-triazolo[3,4-c][1,4]oxazin-4-ium hexa-fluorido-phosphate.

9. 2-Methyl-1,2,4-triazolo[4,3-a]pyridin-2-ium tetra-fluoroborate.

10. Stretching the P-C Bond. Variations on Carbenes and Phosphanes.