Isothiourea‐Catalyzed Functionalization of Pyrrolyl‐ and Indolylacetic Acid: Enantioselective Synthesis of Dihydropyridinones and One‐pot Synthesis of Pyridinones

Zhang, Shuyue; Bacheley, Lucas; Young, Claire M.; Stark, Daniel G.; O’Riordan, Timothy; Slawin, Alexandra M. Z.; Smith, Andrew D.

doi:10.1002/ajoc.202000290

Cited by 8 publications

(1 citation statement)

References 72 publications

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“…After heating at reflux overnight, the resulting solution was cooled to room temperature, followed by the addition of water and extraction with DCM. The combined organic phase was evaporated to dryness and subjected to column chromatography or directly purified through crystallization with AcOEt-hexane 1:1 to generate pure compounds 3 in 50-70% yield with physical and spectroscopic data identical to those reported in literature [41][42][43].…”

Section: General Procedures For N-tosylimine 3 Synthesismentioning

confidence: 95%

Synthesis of 3,4-Dihydropyridin-2-ones via Domino Reaction under Phase Transfer Catalysis Conditions

2023

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3,4-dihydropyridin-2-ones are of considerable importance due to the large number of these core structures exhibiting a diverse array of biological and pharmacological activities. The Michael-type addition of 1,3-dithiane-2-carbothioates to α,β-unsaturated N-tosyl imines, followed by intramolecular annulation driven by a sulfur leaving group, provides a practical reaction cascade for the synthesis of a variety of substituted 3,4-dihydropyridin-2-ones. In this work, the reaction was carried out under solid–liquid phase transfer catalysis (SL-PTC) conditions at room temperature, in short reaction times in the presence of cheap Bu4N+HSO4– and solid KOH. The new PTC method exhibited adequate functional group tolerance, proving to be a green and reliable method and easy to scale up to furnish rapid access to 3,4-dihydropyridin-2-ones after desulfurization from simple, readily available starting materials.

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Section: General Procedures For N-tosylimine 3 Synthesismentioning

confidence: 95%

Synthesis of 3,4-Dihydropyridin-2-ones via Domino Reaction under Phase Transfer Catalysis Conditions

2023

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Isothiourea‐Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6‐ and 1,4‐Additions

et al. 2023

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The enantioselective α‐functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6‐additions to para‐quinone methides (21 examples, up to 95 : 5 dr and 96 : 4 er) and 1,4‐ additions to methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 examples, up to 98 : 2 er). This nucleophilic organocatalysis approach gives access to a range of α‐functionalised α‐amino acid derivatives and further transformations of the activated aryl ester group provide a straightforward entry to advanced amino acid‐based esters, amides or thioesters.

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A One‐Pot Approach to Multi‐Substituted Fused Aziridines: Formal Intermolecular [2+1] Cycloaddition Reaction between Saccharin‐Derived Cyclic Ketimines and Sulfur Ylides

Lin¹,

Wang²,

Wei³

et al. 2023

Eur J Org Chem

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Herein a concise and efficient method for the synthesis of aziridines has been developed. The reaction proceeds through a formal intermolecular [2+1] cycloaddition reaction of saccharin‐derived cyclic ketimines with sulfur ylides. This methodology features high atom‐economy, broad substrate scope and an operationally simple procedure, affording the aziridines with excellent yields and diastereoselectivity (>20 : 1 dr). In the presence of base, the aziridine products could be readily converted to benzothiazines by an unusual rearrangement reaction.

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Isothiourea‐Catalyzed Functionalization of Pyrrolyl‐ and Indolylacetic Acid: Enantioselective Synthesis of Dihydropyridinones and One‐pot Synthesis of Pyridinones

Cited by 8 publications

References 72 publications

Synthesis of 3,4-Dihydropyridin-2-ones via Domino Reaction under Phase Transfer Catalysis Conditions

Synthesis of 3,4-Dihydropyridin-2-ones via Domino Reaction under Phase Transfer Catalysis Conditions

Isothiourea‐Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6‐ and 1,4‐Additions

A One‐Pot Approach to Multi‐Substituted Fused Aziridines: Formal Intermolecular [2+1] Cycloaddition Reaction between Saccharin‐Derived Cyclic Ketimines and Sulfur Ylides

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