A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH<sub>3</sub>OK

Lai, Jingxiong; Huang, You

doi:10.1039/d3cc05751h

Chem. Commun.

2024

DOI: 10.1039/d3cc05751h

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A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH₃OK

Jingxiong Lai,

You Huang

Abstract: The first (5+1) annulation of allenoates and pyrazolones catalyzed by CH3OK has been reported. A series of spiro-pyrazolone derivatives were obtained as a single diastereomer in high yields (≤95%) under...

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Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

Chauhan,

Swamy

2024

J. Org. Chem.

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Dearomative annulation reaction of acyl-tethered benzothiazole bisnucleophiles with β′-acetoxy allenoates by switching the Lewis base is developed. The DBU-catalyzed reaction gives benzothiazole-fused 1,4-dihydropyridine carboxylates by (3 + 3) annulation chemoselectively. By contrast, the PR 3 -catalyzed reaction gives benzothiazole-fused azepines by (4 + 3) annulation and cyclopentene carboxylates by (4 + 1) annulation; the ratio of the latter two products depends on the solvent. A possible rationale for the difference in the reactivity, based on the 1,4/1,5-addition of the 2-acyl−tethered benzothiazole to the key phosphonium intermediate, is provided.

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Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

Chauhan,

Swamy

2024

J. Org. Chem.

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show abstract

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A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH₃OK

Abstract: The first (5+1) annulation of allenoates and pyrazolones catalyzed by CH3OK has been reported. A series of spiro-pyrazolone derivatives were obtained as a single diastereomer in high yields (≤95%) under...

Cited by 1 publication

References 43 publications

Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

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A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH3OK

Abstract: The first (5+1) annulation of allenoates and pyrazolones catalyzed by CH3OK has been reported. A series of spiro-pyrazolone derivatives were obtained as a single diastereomer in high yields (≤95%) under...

Cited by 1 publication

References 43 publications

Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

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A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH₃OK