<i>N</i>-Benzyloxyacrylamides as Bisnucleophiles in an Organocatalyzed Domino aza-Michael/Morita-Baylis-Hillman Sequence

Alahyen, Ismail; Taillier, Catherine; Lhoste, Jérôme; Dalla, Vincent; Comesse, Sébastien

doi:10.1021/acs.orglett.4c00295

Org. Lett.

2024

DOI: 10.1021/acs.orglett.4c00295

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N-Benzyloxyacrylamides as Bisnucleophiles in an Organocatalyzed Domino aza-Michael/Morita-Baylis-Hillman Sequence

Ismail Alahyen,

Catherine Taillier,

Jérôme Lhoste

et al.

Abstract: We herein describe a stereoselective organocatalyzed aza-Michael/Morita-Baylis-Hillman domino reaction between readily accessible acrylamides and α,β-unsaturated carbonyls. This novel, PPh 3 -promoted atom economic one-pot process features medium to good yields and good stereoselectivity leading to variously substituted piperidin-2-ones bearing an exocyclic olefinic bond, which was shown to be an excellent anchor for further chemical diversification.

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Cited by 3 publications

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Chemoselective Intramolecular Rauhut‐Currier Reaction on a Labile Framework of Enone and Acrylamide: Tricyclohexylphosphine as a Stable and Economical Catalyst

Verma,

Bairwa,

Bharadwaj

2024

Eur J Org Chem

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Intramolecular Rauhut‐Currier (IRC) reaction is an atom‐economical way of making carbocyclic and heterocyclic rings. However, its sensitivity towards electronic and steric parameters limits the reaction and stems the need for further development. Acrylamides have been one such left out of their sensitivity. Herein we report an IRC reaction, using acrylamide as a source of initial enolate. The cyclization has been achieved on a labile and challenging framework, prone to decomposition. Different control experiments have addressed the instability of the precursor. Protocol was further extendable to annulation for benzo analogs. We also report tricyclohexylphosphine (PCy3) as a stable, commercial, and easy‐to‐use nucleophilic catalyst in the field of IRC reactions as compared to earlier well‐established trimethyl and tributyl phosphines. Me3P and Bu3P although useful, are sensitive, prone to oxidation, and need careful handling. The protocol leads to the synthesis of piperidone and dihydroquinolone frameworks. A quick study to test the feasibility of catalyzing the Morita‐Baylis‐Hillman (MBH) reaction by PCy3 was also done successfully, although in moderate yields.

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Chemoselective Intramolecular Rauhut‐Currier Reaction on a Labile Framework of Enone and Acrylamide: Tricyclohexylphosphine as a Stable and Economical Catalyst

Verma,

Bairwa,

Bharadwaj

2024

Eur J Org Chem

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Innovative bioinspired hydrogel scaffolds enabling in-situ hybrid nanoflower integration for dual-mode acetylcholinesterase inhibitor profiling

Liu,

Zhang,

Wei

et al. 2024

Biosensors and Bioelectronics

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A Novel 2-Methylimidazole Promoted Oxyacyloxylation of α-Hydroxy Ketones and Anhydrides: An Easy Access to α-Acyloxy Ketones

Yu,

Li,

et al. 2024

Catalysts

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An efficient and operationally simple method for the synthesis of α-acyloxy ketones through the readily available 2-methylimidazole-promoted reaction of α-hydroxy ketones and anhydrides is developed. In the reaction, the anhydrides act as both a substrate and a solvent. The new method features good substrate tolerance, mild reaction conditions, readily accessible starting materials, and excellent yields, providing facile and green access to the targets. Importantly, the reaction also avoids the use of reagents with pungent odors, such as pyridine, in traditional esterification, which may promote the development of organocatalysis using nitrogen-containing heterocyclic compounds as catalysts.

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N-Benzyloxyacrylamides as Bisnucleophiles in an Organocatalyzed Domino aza-Michael/Morita-Baylis-Hillman Sequence

Cited by 3 publications

References 24 publications

Chemoselective Intramolecular Rauhut‐Currier Reaction on a Labile Framework of Enone and Acrylamide: Tricyclohexylphosphine as a Stable and Economical Catalyst

Chemoselective Intramolecular Rauhut‐Currier Reaction on a Labile Framework of Enone and Acrylamide: Tricyclohexylphosphine as a Stable and Economical Catalyst

Innovative bioinspired hydrogel scaffolds enabling in-situ hybrid nanoflower integration for dual-mode acetylcholinesterase inhibitor profiling

A Novel 2-Methylimidazole Promoted Oxyacyloxylation of α-Hydroxy Ketones and Anhydrides: An Easy Access to α-Acyloxy Ketones

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