Gold‐ and Silver‐Catalyzed [4+2] Cycloadditions of Ynamides with Oxetanes and Azetidines

Pawar, Samir Kundlik; Vasu, Dhananjayan; Liu, Rai‐Shung

doi:10.1002/adsc.201400024

Cited by 46 publications

(24 citation statements)

References 59 publications

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“…Alternatively, in the [3+2] cycloaddition, the benzylic cation 679 is obtained due to the stabilization effect of the 4-methoxyphenyl group. In a later study, they reported that oxetanes could also react with ynamides under the catalysis of gold(I) to provide six-membered 6-amino-3,4-dohydro-2 H -pyrans …”

Section: Gold-catalyzed Reactions Of Epoxidesmentioning

confidence: 98%

“…In a later study, they reported that oxetanes could also react with ynamides under the catalysis of gold(I) to provide six-membered 6-amino-3,4-dohydro-2Hpyrans. 168 In 2015, Balamurugan et al reported the Au(I)-catalyzed intermolecular reaction of aryl-and alkyl-substituted epoxides 680 and alkynes 681 in acetone (Scheme 107a). 169 More recently, Liu's group reported the synthesis of 1,4dioxepanes 692 in good yields through the Au(I)-catalyzed [4+3] annulation of t-butyl propiolate derivatives 690 with aryl and alkyl epoxides 691 (Scheme 108a).…”

Section: Gold-catalyzed Reactions Of Aryl Vinyl and Alkyl Aziridinesmentioning

confidence: 99%

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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: Gold-catalyzed Reactions Of Epoxidesmentioning

confidence: 98%

Section: Gold-catalyzed Reactions Of Aryl Vinyl and Alkyl Aziridinesmentioning

confidence: 99%

Gold-Catalyzed Conversion of Highly Strained Compounds

et al. 2020

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“…In these two cycloaddition reactions, azetidines 331 and oxetanes 332 functioned as nucleophiles, whereas metal-p-ynamides functioned as electrophiles (Scheme 95). 244 Another [4+2] cycloaddition of push-pull 1,3-dien-5-ynes 335 and aldimines 336 or silyl aldimines 337 was described 245 This reaction could be mediated either by the catalytic amount of AgSbF 6 alone or by the AuClPEt 3 / AgSbF 6 bimetallic catalyst system, thereby allowing for the regioand diastereoselective formation of trans-5,6-dihydropyridin-2ones 338 and 339 in moderate yields. In contrast to push-pull 1,3-dien-5-ynes 335, the neutral, electron-deficient or electron-rich enynes did not result in dihydropyridones.…”

Section: Cycloadditionmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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Silver is a less expensive noble metal. Superior alkynophilicity due to π-coordination with the carbon-carbon triple bond makes silver salts ideal catalysts for alkyne-based organic reactions. This review highlights the progress in alkyne chemistry via silver catalysis primarily over the past five years (ca. 2010-2014). The discussion is developed in terms of the bond type formed with the acetylenic carbon (i.e., C-C, C-N, C-O, C-Halo, C-P and C-B). Compared with other coinage metals such as Au and Cu, silver catalysis is frequently observed to be unique. This critical review clearly indicates that silver catalysis provides a significant impetus to the rapid evolution of alkyne-based organic reactions, such as alkynylation, hydrofunctionalization, cycloaddition, cycloisomerization, and cascade reactions.

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“…This elegant transformation under mild conditions opened new avenues for gold(I)‐catalyzed (formal) cycloadditions of ynamides. Later on, the same authors reported gold(I)‐ and silver(I)‐catalyzed cycloadditions between ynamides 122 and oxetanes or azetidines, respectively [Scheme , Equations (2) and (3)] …”

Section: [4+2] Cycloadditions Of Ynamidesmentioning

confidence: 99%

Diels–Alder and Formal Diels–Alder Cycloaddition Reactions of Ynamines and Ynamides

et al. 2017

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Nitrogen‐substituted alkynes such as ynamines and ynamides are competent partners in [4+2] cycloaddition reactions. This microreview aims to discuss in a historical context the main achievements in the work on this class of reactions that leads to valuable nitrogen‐containing heterocycles in a single‐step fashion. In the last section, our own work in the field of inverse‐electron‐demand Diels–Alder reactions between ynamides and pyrimidines is discussed.

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Gold‐ and Silver‐Catalyzed [4+2] Cycloadditions of Ynamides with Oxetanes and Azetidines

Cited by 46 publications

References 59 publications

Gold-Catalyzed Conversion of Highly Strained Compounds

Gold-Catalyzed Conversion of Highly Strained Compounds

Silver-catalysed reactions of alkynes: recent advances

Diels–Alder and Formal Diels–Alder Cycloaddition Reactions of Ynamines and Ynamides

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