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Literature DB >> 21905682

Enantioselective synthesis of dihydropyridinones via NHC-catalyzed aza-Claisen reaction.

Benedikt Wanner¹, Jessada Mahatthananchai, Jeffrey W Bode.

Abstract

N-Heterocyclic carbene catalyzed aza-Claisen annulations of enals or their α'-hydroxyenone surrogates with vinylogous amides afford dihydropyridinones. The reaction proceeds with a broad range of substrates, and no nitrogen protecting group is required.

Entities: Chemical Disease

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Year: 2011 PMID： 21905682 DOI： 10.1021/ol202272t

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

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Cited

11 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. 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

3. Oxyanion steering and CH-π interactions as key elements in an N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition.

Authors: Scott E Allen; Jessada Mahatthananchai; Jeffrey W Bode; Marisa C Kozlowski
Journal: J Am Chem Soc Date: 2012-07-16 Impact factor: 15.419

4. Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams.

Authors: Nicholas A White; Daniel A DiRocco; Tomislav Rovis
Journal: J Am Chem Soc Date: 2013-05-28 Impact factor: 15.419

Enantioselective synthesis of dihydropyridinones via NHC-catalyzed aza-Claisen reaction.

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

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

3. Oxyanion steering and CH-π interactions as key elements in an N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition.

4. Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams.

Review 5. A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

6. N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes.

7. N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals.

8. Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.

9. Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine.

10. Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin.