Yb(OTf)<sub>3</sub>‐ or Au<sup>I</sup>‐Catalyzed Domino Intramolecular Hydroamination and Ring‐Opening of Sulfonamide‐Substituted 1,1‐Vinylidenecyclopropanediesters

Wu, Lei; Shi, Min

doi:10.1002/chem.201102159

Cited by 42 publications

(23 citation statements)

References 145 publications

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“…In the proposed mechanism, VDCP 135 is initially activated by the Au(I) complex, followed by a nucleophilic addition of amine to afford intermediate 138 In addition, Shi's group also developed a novel cascade transformation of sulfonamide N−O substituted VDCP-diesters 144 to give ketones 147 (Scheme 26). 62 The mechanism of the reaction involves the allene moiety of VDCP-diester 144 being activated by the cation gold(I)-catalyst. Then an intramolecular hydroamination of the activated allene moeity occurs, along with a ring-opening of cyclopropane to give alkyne intermediate 146.…”

Section: Intermolecular Reactions Of Methylenecyclopropanes (Mcps) Un...mentioning

confidence: 99%

Gold-Catalyzed Conversion of Highly Strained Compounds

et al. 2020

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The past decade has witnessed the golden age of homogeneous gold-catalyzed reactions, especially those that involve the transformation of highly strained molecules into complex molecular architectures. Gold catalysts, with unique electronic properties and catalytic abilities, have elevated versatile reaction modes through π-interaction induced activation. On the basis of increasing research interest in this topic, together with the significant development of various ligands, including phosphine ligands and azacyclic or noncyclic carbene ligands, the understanding of the catalytic function of gold catalysts has become much deeper and more comprehensive. Different reaction needs thus could be adapted by a novel gold catalyst with a diversified ligand selection. Furthermore, the whole evolution of the gold catalysis on synthetic methodologies has realized and expanded its application into natural product synthesis as well as the potentiality of drug discovery, which endows this ancient metal with a magnificent renaissance. The reactivity of strained small ring molecules with high tension has always been an important research topic in organic chemistry. When the highly strained small ring is linked with a π-electron rich moiety or contains a heteroatom, the gold activation of the π-system or coordination with the heteroatom can initiate a cascade reaction, usually followed by ring opening or expansion. These processes can result in the rapid construction of complex and distinct molecular structures, many of which feature in biologically important molecules. In this review, we will mainly summarize the advances on diverse reaction types and molecular constructions accomplished by homogeneous gold catalysis using highly strained substrates, including methylenecyclopropanes (MCPs), vinylidenecyclopropanes (VDCPs), cyclopropenes as well as aziridine- and epoxide-containing molecules, focusing on the last 10 years. For functionalized alkynyl cyclopropanes, several early inspiring and elegant examples will be described in this review for systematically understanding these transformations.

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Section: Intermolecular Reactions Of Methylenecyclopropanes (Mcps) Un...mentioning

confidence: 99%

Gold-Catalyzed Conversion of Highly Strained Compounds

et al. 2020

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“…Shi and Wu reported the Yb(OTf) 3 -catalyzed domino intramolecular hydroamination and ring-opening of sulfonamide-substituted 1,1-vinylidenecyclopropane diesters to yield five-membered N,O-heterocyclic products containing an alkyne moiety in good to excellent yields (Scheme 30). 41 Yb(OTf) 3 was found to be the best catalyst among all Lewis acids screened, including Bi(OTf) 3 , BF 3 •OEt 2 , Ln(OTf) 3 , Sc(OTf) 3 , Ti(Oi-Pr) 4 and HOTf.…”

Section: Scheme 28 Yb(otf) 3 -Catalyzed Synthesis Of 4-arylidene-2-phmentioning

confidence: 96%

Ytterbium Triflate Catalyzed Synthesis of Heterocycles

Sakhuja¹,

Pericherla²,

Bajaj³

et al. 2016

Synthesis

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Ytterbium(III) triflate is an efficient and water-tolerant Lewis acid that has been used as a catalyst for a wide range of organic transformations. Various three-, four-, five-, and six-membered, as well as fused, heterocycles have been synthesized using ytterbium triflate as catalyst in both organic and aqueous solvents. The reaction conditions are relatively mild and the catalyst can be readily recovered from the reaction mixtures to be reused. 1 Introduction 2 Three-Membered Heterocycles 3 Four-Membered Heterocycles 4 Five-Membered Heterocycles 5 Six-Membered Heterocycles 6 Benzo-Fused Heterocycles 7 Non-benzenoid Fused Heterocycles 8 Spiroheterocycles 9 Bridged Heterocycles 10 Conclusion

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“…After the research of Dixon et al [139][140][141], several papers [147][148][149][150][151][152][153][154][155][156][157][158][159][160] nourished the gold-fashion version of P-S cyclization in the years between 2011 and 2015. (2013) The Dixon group developed a high enantioselective N-sulfonyliminium cyclization cascade, which provided complex and unusual sulfonamide scaffolds in excellent yield [148].…”

Section: Au(i)-catalyzed N-acyliminium Cyclization Cascadementioning

confidence: 99%

“…Actually, microwave heating (120 • C) of a mixture of tryptamine (1a, R = H) and o-2-phenylethynyl benzaldehyde (135a, R 1 = Ph) in DCM with 10 mol% of Yb(OTf) 3 after the addition of the ionic liquid [bmim]Cl-AlCl 3 provided the THBC 136 (R = H, R 1 = Ph; 74% yield) within one hour (Scheme 40) [153]. However, the second step, i.e., the hydroamination reaction of the P-S adduct, did not occur in the presence of ytterbium complexes [154,155]. By contrast, after a survey of selected gold complexes, the catalyst EC-1 (10 mol%) (Scheme 37) gave, at room temperature, the desired IQZ 137a (R = H, R 1 = Ph; 62%).…”

Section: Au(i)-catalyzed N-acyliminium Cyclization Cascadementioning

confidence: 99%

The Pictet-Spengler Reaction Updates Its Habits

et al. 2020

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The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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Yb(OTf)₃‐ or Au^I‐Catalyzed Domino Intramolecular Hydroamination and Ring‐Opening of Sulfonamide‐Substituted 1,1‐Vinylidenecyclopropanediesters

Cited by 42 publications

References 145 publications

Gold-Catalyzed Conversion of Highly Strained Compounds

Gold-Catalyzed Conversion of Highly Strained Compounds

Ytterbium Triflate Catalyzed Synthesis of Heterocycles

The Pictet-Spengler Reaction Updates Its Habits

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Yb(OTf)3‐ or AuI‐Catalyzed Domino Intramolecular Hydroamination and Ring‐Opening of Sulfonamide‐Substituted 1,1‐Vinylidenecyclopropanediesters

Cited by 42 publications

References 145 publications

Gold-Catalyzed Conversion of Highly Strained Compounds

Gold-Catalyzed Conversion of Highly Strained Compounds

Ytterbium Triflate Catalyzed Synthesis of Heterocycles

The Pictet-Spengler Reaction Updates Its Habits

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Product

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Yb(OTf)₃‐ or Au^I‐Catalyzed Domino Intramolecular Hydroamination and Ring‐Opening of Sulfonamide‐Substituted 1,1‐Vinylidenecyclopropanediesters