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Literature DB >> 19724784

Recent development of reactions with alpha-diazocarbonyl compounds as nucleophiles.

Abstract

The nucleophilic addition reaction of diazo-compound derived anions or enolates with electrophilic C=O and C=N bonds have been summarized. The subsequent reactions of the addition products demonstrate diverse reactivities of the diazocarbonyl compounds bearing other functional groups and their potential in organic synthesis. Asymmetric catalysis is also possible with diazocarbonyl compounds as nucleophiles.

Entities: Chemical

Mesh：

Substances：
Azo Compounds

Year: 2009 PMID： 19724784 DOI： 10.1039/b908378b

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

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Cited

9 in total

1. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

Authors: Alexey Kuznetsov; Anton V Gulevich; Donald J Wink; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2014-07-01 Impact factor: 15.336

2. Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Authors: Thomas P Willumstad; Olesya Haze; Xiao Yin Mak; Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal: J Org Chem Date: 2013-10-28 Impact factor: 4.354

3. 1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides.

Authors: Matthew R Aronoff; Brian Gold; Ronald T Raines
Journal: Org Lett Date: 2016-03-16 Impact factor: 6.005

4. Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.

Authors: Anton V Gulevich; Victoria Helan; Donald J Wink; Vladimir Gevorgyan
Journal: Org Lett Date: 2013-02-01 Impact factor: 6.005

Recent development of reactions with alpha-diazocarbonyl compounds as nucleophiles.

1. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

2. Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

3. 1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides.

4. Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.

5. Rh-catalyzed Reagent-Free Ring Expansion of Cyclobutenones and Benzocyclobutenones.

6. Asymmetric synthesis of CF₂-functionalized aziridines by combined strong Brønsted acid catalysis.

7. Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles.

8. Selective Synthesis of Azoloyl NH-1,2,3-Triazoles and Azolyl Diazoketones: Experimental and Computational Insights.

Review 9. From reactive carbenes to chiral polyether macrocycles in two steps - synthesis and applications made easy?