Organic Transformations with
            <scp>MeNO</scp>
            <sub>2</sub>

Das, Debarati; Patil, Nilam; Bhanage, Bhalchandra M.

doi:10.1002/9783527831883.ch32

The Chemical Transformations of C1 Compounds 2022

DOI: 10.1002/9783527831883.ch32

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Organic Transformations with MeNO ₂

Debarati Das

Nilam Patil

Bhalchandra M. Bhanage

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2024

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Cited by 2 publications

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“…Beyond being used as a well-known polar organic solvent, nitromethane also serves as a versatile precursor in organic chemistry . Due to the strong electron-withdrawing nature of the nitro group, nitromethane has often been used as a source of nucleophilic nitroalkanes in various transformations.…”

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confidence: 99%

Asymmetric Tandem Michael Addition/Interrupted Nef Reactions of Nitromethane with Oxindole-Derived Alkenes: Enantioselective Synthesis of Spiro-polycyclic Oxindoles

Liu,

Yang,

Yang

et al. 2024

Org. Lett.

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Chiral spiro-polycyclic oxindoles are valuable heterocyclic ring systems that are widely distributed in natural alkaloids and biologically active compounds. Herein, we reported an asymmetric tandem Michael addition/interrupted Nef reaction of nitromethane with oxindole-derived alkenes catalyzed by a chiral 2-aminobenzimidazole bifunctional organocatalyst. A series of novel enantiomerically enriched spiro-polycyclic oxindole derivatives bearing an oxime group were synthesized in moderate to excellent isolated yields (up to 99%) with an excellent level of enantioselectivities (up to 99% ee). Furthermore, the antiproliferation activity of the resulting oxindoles derivatives were evaluated, and compound 2d demonstrated promising anticancer properties against HCT116 (IC 50 = 14.08 μM) and HT29 (IC 50 = 15.46 μM) cell lines.

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mentioning

confidence: 99%

Asymmetric Tandem Michael Addition/Interrupted Nef Reactions of Nitromethane with Oxindole-Derived Alkenes: Enantioselective Synthesis of Spiro-polycyclic Oxindoles

Liu,

Yang,

Yang

et al. 2024

Org. Lett.

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Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

2022

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Recursive Anionic Cyclization (RAC) continues to proliferate as a mechanistically distinct domino strategy. Deployment of nitroalkanes as a source of recursive carbanions has created a niche operating space for generating molecular complexity and diversity. This new corollary i. e. recursive nitronate cyclization is the basis of a domino [5 C+1 C] cyclization strategy wherein nitroalkanes act as one‐carbon lynchpin, providing rapid access to topologically intriguing, densely functionalized carbo‐ and heterocycles embodying multiple chiral centers with regio‐, stereo‐ and enantioselectivity. Extension to aromatic domains, particularly via benzannulation reactions, has further consolidated the operating space. While leveraging the functional versatility of nitro group for post‐domino modifications, such endeavors have culminated in total synthesis of diverse natural products. An incisive analysis of recursive nitronate cyclizations and their emergent potentials is delineated in this review. It is hoped that this focused narrative will enthuse and draw new practitioners to the arena to advance the field.

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Organic Transformations with MeNO ₂

Cited by 2 publications

References 253 publications

Asymmetric Tandem Michael Addition/Interrupted Nef Reactions of Nitromethane with Oxindole-Derived Alkenes: Enantioselective Synthesis of Spiro-polycyclic Oxindoles

Asymmetric Tandem Michael Addition/Interrupted Nef Reactions of Nitromethane with Oxindole-Derived Alkenes: Enantioselective Synthesis of Spiro-polycyclic Oxindoles

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

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Organic Transformations with MeNO 2

Cited by 2 publications

References 253 publications

Asymmetric Tandem Michael Addition/Interrupted Nef Reactions of Nitromethane with Oxindole-Derived Alkenes: Enantioselective Synthesis of Spiro-polycyclic Oxindoles

Asymmetric Tandem Michael Addition/Interrupted Nef Reactions of Nitromethane with Oxindole-Derived Alkenes: Enantioselective Synthesis of Spiro-polycyclic Oxindoles

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

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Product

Resources

About

Organic Transformations with MeNO ₂