Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo <i>γ</i>-Pyrones and Diazo 3(2<i>H</i>)-Furanones

In AgSbF6/Rh2(OAc)4/DCM system, two‐component reaction of 2‐diazo‐3,5‐dioxo‐6‐ynoates (sulfones) and two equivalent of aldehydes provided easy access to 2‐(1,3‐dioxolanes‐4‐yl)‐4H‐pyran‐4‐ones. This represents the first method for generating the novel heterocyclic compounds. A possible mechanism is proposed to explain this result. The most significant features of the tandem cyclization are simple procedure, mild conditions and high diastereoselectivity.

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Diastereoselective Synthesis of 2‐(1,3‐Dioxolanes‐4‐yl)‐4H‐pyran‐4‐ones from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (sulfones) and Aldehydes Based on Tandem Cyclization‐Cycloaddition Strategy

Zhang

Deng

Wang

2019

Eur J Org Chem

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Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines

et al. 2019

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On the basis of a tandem strategy, AgSbF6/Rh2(OAc)4/Ag3PO4‐mediated reaction of 2‐diazo‐3,5‐dioxo‐6‐ynoate (ynones) with N,N‐disubstituted anilines or aza‐aromatic hydrocarbons afforded a series of 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2‐(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones). For N‐allyl‐N‐substituted aniline, the corresponding cyclopropanation did not occurred. Disymmetric 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates were also obtained in good yield from 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates and N,N‐disubstituted anilines (or aza‐aromatic hydrocarbons) by C(sp3)–C(sp2) cross‐coupling reaction. AgSbF6/Ag3PO4 plays a key role in the C(sp3)–C(sp2) cross‐coupling reaction. This unique synthetic method for synthesis of two desired products starting from identical materials was proved to be efficient except for N‐substituted aniline.

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Synthesis of 4H-cyclopenta[c]furan-5(6H)-one derivatives

Peng

Deng

2020

Tetrahedron

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Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones

Cited by 5 publications

References 4 publications

Diastereoselective Synthesis of 2‐(1,3‐Dioxolanes‐4‐yl)‐4H‐pyran‐4‐ones from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (sulfones) and Aldehydes Based on Tandem Cyclization‐Cycloaddition Strategy

Diastereoselective Synthesis of 2‐(1,3‐Dioxolanes‐4‐yl)‐4H‐pyran‐4‐ones from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (sulfones) and Aldehydes Based on Tandem Cyclization‐Cycloaddition Strategy

Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines

Synthesis of 4H-cyclopenta[c]furan-5(6H)-one derivatives

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