A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α‐Ketoesters

Murauski, Kathleen J. R.; Walden, Daniel M.; Cheong, Paul Ha Yeon; Scheidt, Karl A.

doi:10.1002/adsc.201701015

Cited by 17 publications

(7 citation statements)

References 89 publications

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“…Aldehydes 91 were converted into the corresponding substituted chiral γ-butyrolactones 178 in good yields and high enantioselectivities of up to 95% (Scheme 70 ). 136b…”

Section: Enantioselective Organocatalytic Reactionsmentioning

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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“…Aldehydes 91 were converted into the corresponding substituted chiral γ-butyrolactones 178 in good yields and high enantioselectivities of up to 95% (Scheme 70 ). 136b…”

Section: Enantioselective Organocatalytic Reactionsmentioning

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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“…In an analogous multicatalysis, the enantioselective lactonization 72 generated from the simple enanls 23 and α ‐ketoesters 71 , which has been discovered using a new ternary cooperative catalytic system (Scheme 18). [35] The highly selective annulation was achieved by using a combination of a chiral NHC, a hydrogen bond donor, and a metal salt, facilitating the self‐assembly of the reactive partners. This dual catalytic system could improve both reaction yield and enantioselectivity.…”

Section: Cocatalyzed Reaction Involving Nhc and Hydrogen‐bond Donormentioning

confidence: 99%

Enantioselective Dual Catalysis of N‐Heterocyclic Carbene and Hydrogen‐Bond Donor Organocatalysts

2022

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N-heterocyclic carbene (NHC) catalysis has become a versatile catalysis strategy for building molecules via unique reaction modes. Dual catalytic processes using NHCs in combination with additional modulating agents such as another organocatalyst or transition-metal catalyst have also been studied. The clear selection of cocatalysts has led to enhanced reactivity, increased yields, and/or improved stereoselectivity. This minireview is to provide readers with a brief overview of the development and applications of NHC and hydrogen-bond donor for dual catalytic reactions.

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“…60 In this context, Scheidt and co-workers reported a biorgano/metal-catalyzed enantioselective lactonization of unsaturated aldehyde 276 with α-ketoester 277 in order to furnish highly desirable γ-butyrolactone 278 in excellent ee (Scheme 39). 61 Critical parameters like π-stacking, conformation of thiourea, bridging of the nucleophile and electrophile, among others, which are directly affiliated to enantiodiscriminating transition state 279 were thoroughly studied. This highly ordered transition state 279 comprising a network of all the catalysts was supported by NMR studies.…”

Section: Ternary Catalysismentioning

confidence: 99%

Ternary Catalysis: A Stepping Stone toward Multicatalysis

et al. 2020

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The endeavor of mastering “Nature-like Multicatalysis” in vitro has inspired chemists to develop catalytic systems comprising a variable number of catalysts in one-pot. Having been pioneered in the primitive stages (particularly unary and binary catalysis), the field has witnessed the inception of “Ternary Catalysis” described as the concept of harnessing an ensemble effect of three discrete catalysts in one-pot. Although the concept is nascent, it has already demonstrated its invaluable importance in terms of producing novel reactivity, prodigious selectivity, and efficiency. As evident from the presented documentation, the number of pertinent reports utilizing ternary catalysis has drastically increased in the past few years; however, these reports remain scattered in the literature. The conceptualization and unambiguous catalyst-dependent classification presented herein provides an imperative unified approach to assemble and categorize all such reports which have remained missing by far. Special emphasis has been given to mechanistic analysis clearly disclosing the beauty of ternary catalysis. For the better understanding of the concept, a succinct description of challenges and problems associated in the development of a ternary catalytic system has been presented. In addition, the Review briefly discusses some of the unsolved problems and possible developments in this field.

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A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α‐Ketoesters

Cited by 17 publications

References 89 publications

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

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

Enantioselective Dual Catalysis of N‐Heterocyclic Carbene and Hydrogen‐Bond Donor Organocatalysts

Ternary Catalysis: A Stepping Stone toward Multicatalysis

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