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Literature DB >> 18759433

N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters.

Abstract

N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield. The reaction proceeds through a transient activated alcohol, which when generated in situ allows for the selective oxidation of the aldehyde under mild conditions. These conditions successfully oxidize potentially epimerizable aldehydes and alcohols while preserving stereochemical integrity. A variety of ester derivatives can be synthesized with variation of the acylated alcohol as well as the unactivated aldehyde.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2008 PMID： 18759433 PMCID： PMC2657179 DOI： 10.1021/ol8018488

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

20 in total

1. Tandem oxidation processes using manganese dioxide: discovery, applications, and current studies.

Authors: Richard J K Taylor; Mark Reid; Jonathan Foot; Steven A Raw
Journal: Acc Chem Res Date: 2005-11 Impact factor: 22.384

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. A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes.

Authors: Eric M Phillips; Manabu Wadamoto; Audrey Chan; Karl A Scheidt
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

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. N-heterocyclic carbenes as organocatalysts.

Authors: Nicolas Marion; Silvia Díez-González; Steven P Nolan
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

6. Conversion of alpha,beta-unsaturated aldehydes into saturated esters: an Umpolung reaction catalyzed by nucleophilic carbenes.

Authors: Audrey Chan; Karl A Scheidt
Journal: Org Lett Date: 2005-03-03 Impact factor: 6.005

7. Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes.

Authors: Brooks E Maki; Audrey Chan; Eric M Phillips; Karl A Scheidt
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

8. Peroxovanadium-catalyzed oxidative esterification of aldehydes.

Authors: Rangam Gopinath; Balaka Barkakaty; Bandana Talukdar; Bhisma K Patel
Journal: J Org Chem Date: 2003-04-04 Impact factor: 4.354

Review 9. One-pot oxidative esterification and amidation of aldehydes.

Authors: Kekeli Ekoue-Kovi; Christian Wolf
Journal: Chemistry Date: 2008 Impact factor: 5.236

10. Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors: Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal: J Am Chem Soc Date: 2007-07-31 Impact factor: 15.419

21 in total

N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters.

1. Tandem oxidation processes using manganese dioxide: discovery, applications, and current studies.

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

3. A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes.

Review 4. Organocatalysis by N-heterocyclic carbenes.

5. N-heterocyclic carbenes as organocatalysts.

6. Conversion of alpha,beta-unsaturated aldehydes into saturated esters: an Umpolung reaction catalyzed by nucleophilic carbenes.

7. Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes.

8. Peroxovanadium-catalyzed oxidative esterification of aldehydes.

Review 9. One-pot oxidative esterification and amidation of aldehydes.

10. Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

1. Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

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

3. High-throughput photocapture approach for reaction discovery.

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

5. Pd-catalyzed aldehyde to ester conversion: a hydrogen transfer approach.

Review 6. A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

7. Impact of solvent polarity on N-heterocyclic carbene-catalyzed beta-protonations of homoenolate equivalents.

8. Single-flask synthesis of N-acylated indoles by catalytic dehydrogenative coupling with primary alcohols.

9. Total Synthesis of Clavosolide A via Tandem Allylic Oxidation/Oxa-Conjugate Addition Reaction.

10. Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids.