Recent developments in gold-catalyzed cycloaddition reactions

López, Fernándo; Mascareñas, José L.

doi:10.3762/bjoc.7.124

Cited by 182 publications

(36 citation statements)

References 107 publications

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“…However, in recent years, more and more Au- and Pt-catalyzed cycloadditions have been developed. 4, 5 These new discoveries then fed back in to the loop and inspired the development of recent Rh-catalyzed cycloadditions in this article.…”

Section: Introductionmentioning

confidence: 89%

Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

et al. 2012

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Transition metal-catalyzed acyloxy migration of propargylic esters offers versatile entries to allene and vinyl carbene intermediates for various fascinating subsequent transformations. Most π-acidic metals (e.g. gold and platinum) are capable of facilitating these acyloxy migration events. However, very few of these processes involve redox chemistry, which are well-known for most other transition metals such as rhodium. The coupling of acyloxy migration of propargylic esters with oxidative addition, migratory insertion, and reductive elimination may lead to ample new opportunities for the design of new reactions. This tutorial review summarizes recent developments in Rh-catalyzed 1,3- and 1,2-acyloxy migration of propargylic esters in a number of cycloaddition reactions. Related Au- and Pt-catalyzed cycloadditions involving acyloxy migration are also discussed.

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Section: Introductionmentioning

confidence: 89%

Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

et al. 2012

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“…In some cases, experimental and theoretical evidence supports the participation of one of those structures, but in many other cases the precise nature of these species remains unknown. The gold-activated allene complexes have been shown to participate in a great variety of intra- and intermolecular cycloaddition reactions, including [4 + 3], [4 + 2], [3 + 3], [3 + 2] or [2 + 2] annulation processes [1–10 24–26]. Particular attention has been paid during the last years to the development of enantioselective versions of these processes by using chiral gold catalysts.…”

Section: Reviewmentioning

confidence: 99%

“…Especially relevant in terms of synthetic practicality are cycloadditions which are catalyzed by transition metal complexes [19–23]. In particular, gold(I) complexes, owing to their high carbophilicity, low oxophilicity and high oxidation potential between gold(I) and gold(III) have shown a unique potential to unveil novel types of chemoselective and stereoselective cycloadditions involving alkynes, allenes or alkenes [24–26]. …”

Section: Introductionmentioning

confidence: 99%

Gold(I)-catalyzed enantioselective cycloaddition reactions

López

Mascareñas

2013

Beilstein J. Org. Chem.

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109

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In recent years there have been extraordinary developments of gold(I)-catalyzed enantioselective processes. This includes progress in the area of cycloaddition reactions, which are of particular interest due to their potential for the rapid construction of optically active cyclic products. In this article we will summarize some of the most remarkable examples, emphasizing reaction mechanisms and key intermediates involved in the processes. 2250

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“…[1] These reactions focus intensively on electron-rich ynamides, [2] and recently on electron-deficient propiolates. [1] These reactions focus intensively on electron-rich ynamides, [2] and recently on electron-deficient propiolates.…”

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confidence: 99%

Development of Gold‐catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

Sahani

Liu

2016

Angewandte Chemie

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Tw on ew gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial Oattackonthe alkyne to afforda[4+ +1] annulation product. This process results in ar emarkable alkyne cleavage of initial propiolates.U nsubstituted isoxazoles proceed through an Nattacks tep to yield formal [2+ +2+ +1]/[4+ +2] annulation products.T hese two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.Supportinginformation for this article can be found under: http://dx.

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Recent developments in gold-catalyzed cycloaddition reactions

Abstract: SummaryIn the last years there have been extraordinary advances in the development of gold-catalyzed cycloaddition processes. In this review we will summarize some of the most remarkable examples, and present the mechanistic rational underlying the transformations.

Cited by 182 publications

References 107 publications

Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

Gold(I)-catalyzed enantioselective cycloaddition reactions

Development of Gold‐catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

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