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Literature DB >> 19170540

An efficient carbene-catalyzed access to 3,4-dihydrocoumarins.

Abstract

Dihydrocoumarins play an important role as flavor and fragrance compounds and can be prepared efficiently from o-hydroxycinnamaldehydes in a mild, atom-economic N-heterocyclic carbene-catalyzed redox lactonization. Corresponding coumarins are accessible via a one-pot domino oxidation lactonization procedure in the presence of oxidants.

Entities: Chemical Disease

Year: 2009 PMID： 19170540 DOI： 10.1021/jo802285r

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

9 in total

1. A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Authors: Kun Liu; M Todd Hovey; Karl A Scheidt
Journal: Chem Sci Date: 2014-10-01 Impact factor: 9.825

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

Authors: Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal: Aldrichimica Acta Date: 2009 Impact factor: 3.667

3. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors: Anna Lee; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-25 Impact factor: 6.222

4. 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

An efficient carbene-catalyzed access to 3,4-dihydrocoumarins.

1. A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

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

3. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

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

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

6. Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles.

7. (E)-2-Hy-droxy-cinnamaldehyde.

8. Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach.

9. Crystal structure of (E)-3-(5-bromo-2-hydroxy-phen-yl)acryl-aldehyde.