Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO

Brancour, Célia; Fukuyama, Takahide; Ohta, Yuko; Ryu, Ilhyong; Dhimane, Anne Lise; Fensterbank, Louis; Malacrìa, Max

doi:10.1039/c0cc00747a

Cited by 73 publications

(34 citation statements)

References 36 publications

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“…23 ACE was recently also employed as a 5C synthon in a novel Rh(I)-catalyzed [5+1] cycloaddition with CO for the synthesis of highly substituted phenols. 24 …”

Section: Introductionmentioning

confidence: 99%

Rhodium-Catalyzed Intra- and Intermolecular [5 + 2] Cycloaddition of 3-Acyloxy-1,4-enyne and Alkyne with Concomitant 1,2-Acyloxy Migration

Shu

et al. 2012

J. Am. Chem. Soc.

100

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A new type of rhodium-catalyzed [5+2] cycloaddition was developed for the synthesis of seven-membered rings with diverse functionalities. The ring formation was accompanied by a 1,2-acyloxy migration event. The 5- and 2-carbon components of the cycloaddition are 3-acyloxy-1,4-enynes (ACEs) and alkynes respectively. Cationic rhodium (I) catalysts worked most efficiently for the intramolecular cycloaddition, while only neutral rhodium (I) complexes could facilitate the intermolecular reaction. In both cases, electron-poor phosphite or phosphine ligands often improved the efficiency of the cycloadditions. The scope of ACEs and alkynes was investigated in both intra- and intermolecular reactions. The resulting seven-membered ring products have three double bonds that could be selectively functionalized.

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“…23 ACE was recently also employed as a 5C synthon in a novel Rh(I)-catalyzed [5+1] cycloaddition with CO for the synthesis of highly substituted phenols. 24 …”

Section: Introductionmentioning

confidence: 99%

Rhodium-Catalyzed Intra- and Intermolecular [5 + 2] Cycloaddition of 3-Acyloxy-1,4-enyne and Alkyne with Concomitant 1,2-Acyloxy Migration

Shu

et al. 2012

J. Am. Chem. Soc.

100

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“…It has been demonstrated that 3-acyloxy-1,4-enynes with a terminal alkyne can serve as a five-carbon building block for [5+1] [157] and [5+2] [158] cycloadditions with CO and alkynes, respectively. Moreover, both of these cycloadditions involve a rhodium-catalyzed 1,2-acyloxy migration of propargyl esters which was reported in 1984 [159,160].…”

Section: %mentioning

confidence: 99%

Rhodium-Catalyzed Carbonylative Synthesis of Heterocycles

Feng¹,

Wu²

2015

Topics in Heterocyclic Chemistry

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“…56, 65 This method provided access to various functionalized resorcinol derivatives from readily available 3-acyloxy-1,4-enynes.…”

Section: Cycloadditions Involving Rh-catalyzed 12-acyloxy Migratimentioning

confidence: 99%

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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Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO

Cited by 73 publications

References 36 publications

Rhodium-Catalyzed Intra- and Intermolecular [5 + 2] Cycloaddition of 3-Acyloxy-1,4-enyne and Alkyne with Concomitant 1,2-Acyloxy Migration

Rhodium-Catalyzed Intra- and Intermolecular [5 + 2] Cycloaddition of 3-Acyloxy-1,4-enyne and Alkyne with Concomitant 1,2-Acyloxy Migration

Rhodium-Catalyzed Carbonylative Synthesis of Heterocycles

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

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