Bis(amino)cyclopropenylidene Catalyzed Rauhut–Currier Reaction between α,β-Unsaturated Carbonyl Compounds and <i>para</i>-Quinone Methides

Goswami, Prithwish; Sharma, Sonam; Singh, Gurdeep; Anand, Ramasamy Vijaya

doi:10.1021/acs.joc.8b00225

Cited by 52 publications

(20 citation statements)

References 77 publications

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“…Surprisingly, despite these opportunities, NHCs have received limited attention in RC catalysis . Specifically, in 2018, Anand and co‐workers introduced a non‐enantioselective intermolecular RC reaction, with two low‐yielding enoate‐enone example. The groups of Scheidt and Chi have reported elegant, and mechanistically distinct, RC reactions exploiting NHCs as cooperative catalysts or initiators.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective N‐Heterocyclic Carbene Catalyzed Bis(enoate) Rauhut–Currier Reaction

et al. 2019

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While the enantioselective Rauhut–Currier reaction is established with bis(enone) substrates, it is yet to be reported with less electrophilic bis(enoate) substrates. By exploiting high‐nucleophilicity N‐heterocyclic carbenes, it is possible to achieve Rauhut–Currier reactions with these substrates. The reaction is demonstrated with a range of intramolecular reactions (20 examples) and six esterification/RC reaction cascades, which all proceed with high enantioselectivity (most >93:7 er).

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Section: Methodsmentioning

confidence: 99%

Enantioselective N‐Heterocyclic Carbene Catalyzed Bis(enoate) Rauhut–Currier Reaction

et al. 2019

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“…First we have performed our standard reaction by using phenanthrene-9-carbaldehyde (11 a, 0.24 mmol) and 2,6-di-tert-butylphenol (0.504 mmol) to afford triaryl product (11 b, 78 %). Follow-up Further, selective dealkylation [29] and O-methylation [30] of the hydroxy groups led to the formation of 11 c. Thereafter, 11 c performed O-alkylation by using 2-chloro-N,N-dimethylethanamine under the action of K 2 CO 3 to afford anti-breast cancer agent (11 d, 86 %, Scheme 10). [10] These results indicate that this method can provide facile access to biologically active compounds and can be employed to generate unique chemical libraries that are based on triarylmethanes for the screening of biologically active compounds.…”

Section: Synthesis Of Bio-active Moleculesmentioning

confidence: 99%

Development of Transition‐Metal‐Free Lewis Acid‐Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti‐Breast‐Cancer Agent

Singh

Mahato

Sharma

et al. 2022

Chemistry A European J

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This work describes a mild and robust double hydroarylation strategy for the synthesis of symmetrical /unsymmetrical diaryl-and triarylmethanes in excellent yields using Lambert salt (0.2-1.0 mol%). Despite the anticipated challenges associated with controlling selective product formation, unsymmetrical diaryl-and triarylmethanes products are obtained unprecedentedly. A highly efficient gram scale reaction has also been reported (TON for symmetrical product = 475 and for unsymmetrical product = 390). The synthetic utility of the methodology is demonstrated by the preparation of several unexplored diaryl-and triarylmethanebased biologically relevant molecules, such as arundine, vibrindole A, turbomycin B, and certain anti-inflammatory agents. A total synthesis of an anti-breast-cancer agent is also demonstrated. Control experiments, Hammett analysis, HRMS and GC-MS studies reveal the reaction intermediates and reaction mechanism.

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“…The reaction involves the coupling between an active alkene and Michael acceptor. 172 Later, in 2019 the group of Lupton reported an intramolecular Rauhut-Carrier reaction via highly nucleophilic NHC catalysts M3, and bis(enolate) 139 was used as substrate. The reaction mechanism involves the synthesis of an enolate, that cyclizes to lactone.…”

Section: Enantioselective Rauhut-currier Reactionmentioning

confidence: 99%

Recent Advances in Enantioselective Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes (NHCs) Containing Triazolium Motifs

Sharma¹,

Chatterjee

Dhayalan

et al. 2022

Synthesis

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N-Heterocyclic carbenes (NHCs) containing triazolium motifs have emerged as a powerful tool in organocatalysis. Recently, various NHC pre-catalyst mediated organic transformations have been developed successfully. This article aims to compile the current state of knowledge on NHC-triazolium catalysed enantioselective name reactions and introduce newly developed catalytic methods. Furthermore, this review article framework provides an excellent opportunity to highlight some of the unique applications of these catalytic procedures in the natural product synthesis of biologically active compounds, notably the wide range of preparation of substituted chiral alcohols, and their derivatives. This article provides an overview of chiral NHC triazolium-catalyst libraries synthesis and their catalytic application in enantioselective reactions.

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Bis(amino)cyclopropenylidene Catalyzed Rauhut–Currier Reaction between α,β-Unsaturated Carbonyl Compounds and para-Quinone Methides

Abstract: An intermolecular Rauhut-Currier reaction between α,β-unsaturated carbonyl compounds and p-quinone methides has been developed by employing bis(amino)cyclopropenylidene as a catalyst. This protocol allows access to a variety of vinyl diarylmethane derivatives in moderate to good yields.

Cited by 52 publications

References 77 publications

Enantioselective N‐Heterocyclic Carbene Catalyzed Bis(enoate) Rauhut–Currier Reaction

Enantioselective N‐Heterocyclic Carbene Catalyzed Bis(enoate) Rauhut–Currier Reaction

Development of Transition‐Metal‐Free Lewis Acid‐Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti‐Breast‐Cancer Agent

Recent Advances in Enantioselective Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes (NHCs) Containing Triazolium Motifs

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