Phosphine-catalyzed Rauhut–Currier reaction of γ-alkyl allenoate and subsequent trapping using the Diels–Alder reaction

Zhang, Juan; Hao, Wei; Chen, Ying; Wang, Zhen; Yao, Jinzhong; Yao, Weijun

doi:10.1039/d3cc03151a

Chem. Commun.

2023

DOI: 10.1039/d3cc03151a

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Phosphine-catalyzed Rauhut–Currier reaction of γ-alkyl allenoate and subsequent trapping using the Diels–Alder reaction

Juan Zhang,

Wei Hao,

Ying Chen

et al.

Abstract: We have disclosed a Rauhut–Currier reaction of γ-alkyl-substituted allenoate, catalyzed by l-valine-derived amide phosphine, to form trisubstitued allenoate, which was trapped by maleimide or DMAD via the Diels–Alder reaction.

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2024

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Cited by 3 publications

References 49 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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show abstract

Phosphine-catalyzed enantioselective and diastereodivergent [3+2] cyclization for the construction of oxetane dispirooxindole skeletons

Han,

Hou,

Zhang

et al. 2024

Chem. Commun.

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Concise Synthesis of Tetrasubstituted 1,6-Dihydropyridazine and Pyridazine Derivatives

Zhang,

Wang

et al. 2024

Synthesis

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We have developed a novel one pot three steps process, including phosphine catalyzed Rauhut−Currier reaction of γ-alkyl allenoate, Diels-Alder reaction with di-tert-butyl azodicarboxylate and followed by deprotection of Boc group, to prepared tetra-substituted 1,6-dihydropyridazine in good yield. The 1,6-dihydropyridazine was easily converted to pyridazine derivatives via oxidative aromatization by DDQ.

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Phosphine-catalyzed Rauhut–Currier reaction of γ-alkyl allenoate and subsequent trapping using the Diels–Alder reaction

Abstract: We have disclosed a Rauhut–Currier reaction of γ-alkyl-substituted allenoate, catalyzed by l-valine-derived amide phosphine, to form trisubstitued allenoate, which was trapped by maleimide or DMAD via the Diels–Alder reaction.

Cited by 3 publications

References 49 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

Phosphine-catalyzed enantioselective and diastereodivergent [3+2] cyclization for the construction of oxetane dispirooxindole skeletons

Concise Synthesis of Tetrasubstituted 1,6-Dihydropyridazine and Pyridazine Derivatives

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