The Nef Reaction of Isocyanides

A new and flexible methodology catalyzed by bifunctional chiral thioureas has been developed to react β-nitro oxindoles 1 with aldehydes. This approach allowed us to achieve the first enantioselective organocatalytic synthesis of 3-spiro-α-alkylidene-γ-butyrolactone oxindoles 3. We examined the scope of the two starting materials and, varying the structure of the β-nitro oxindole 1, intriguing new products, derived from unexpected transformations, have been stereoselectively obtained. The aim of this study was to merge two potentially bioactive structural motifs: the spirooxindole substructure and the α-alkylidene-γ-butyrolactone moiety. A preliminary NMR study on the ability to reversibly trap 2-aminoethanethiol gave us promising results.

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The First Enantioselective Organocatalytic Synthesis of 3‐Spiro‐α‐Alkylidene‐γ‐Butyrolactone Oxindoles

Cerisoli

Lombardo

Trombini

et al. 2016

Chemistry A European J

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ChemInform Abstract: The Nef Reaction of Isocyanides

Spisa¹,

Tron²,

Kaı̈m

2014

ChemInform

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Origins of the Reactivity in 1,3‐Dipolar Cycloadditions of Acyl Isocyanide Ylides

et al. 2022

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1,3-Dipolar cycloadditions are the preferred method to generate five-membered heterocyclic rings. Surprisingly, cycloadditions based on acyl-isocyanide ylides have remained underexplored by the chemical community. Acyl-isocyanide ylides readily react with dipolarophiles, such as substituted alkenes, to yield Δ 1pyrroline derivatives. As an explanation for the observed reactivity of this reaction is lacking, extensive density functional theory calculations were performed to scrutinize the mechanistic features of the transformation. Herein we explain the experimental outcome of the reaction using a variety of reactivity theories and predict opposed regioselectivity for electron-poor and electron-rich dipolarophiles. With the insights obtained, we hope to incentivize the design of new cycloaddition reactions based on the acyl-isocyanide ylides motif.

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The Nef Reaction of Isocyanides

Cited by 18 publications

References 32 publications

The First Enantioselective Organocatalytic Synthesis of 3‐Spiro‐α‐Alkylidene‐γ‐Butyrolactone Oxindoles

The First Enantioselective Organocatalytic Synthesis of 3‐Spiro‐α‐Alkylidene‐γ‐Butyrolactone Oxindoles

ChemInform Abstract: The Nef Reaction of Isocyanides

Origins of the Reactivity in 1,3‐Dipolar Cycloadditions of Acyl Isocyanide Ylides

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