Gold-catalyzed cyclizations of alkyne propargylic acetates to 2,3-bis(alkylidene)cycloalkanones and their related benzene derivatives

Oh, Chang Ho; Kim, Ahyun

doi:10.1039/b705320g

Cited by 52 publications

(17 citation statements)

References 23 publications

(2 reference statements)

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“…Toste et al reported silver-catalyzed 1,3-acyl migration of a nonterminal propargylic esters (Type A) to the highly functionalized aromatic compounds (Type A1). 12 During our study, the standard conditions towards alkynes-propargylic acetates like D did not afford the expected diene products, but exhibited a different mode of reactions to give the [n,2,0]bicyclic products like D2. 6 Next, Liu group has reported about a goldcatalyzed allene formation via 1,3-acyl migration of a propargyl carbonates (Type A1).…”

Section: Introductionmentioning

confidence: 65%

Synthesis of Primitive Dendrimer Systems Bearing Bicyclo[3,2,0]Hept‐6‐en‐6‐yl Groups via Unique Au‐catalyzed [2+2] Cyclization

Lee

Jillella

Kim

et al. 2018

Bulletin Korean Chem Soc

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Propargylic pivaloates bearing an alkynyl group at a three-carbon tether under the gold catalysis would undergo [3,3] rearrangements of propargylic pivaloates followed by tandem [2+2] cyclization to give the corresponding 6-acylbicyclo[3,2,0]hept-6-ens. In continuing work, we prepared various substrates bearing two arms of alkyne-propargylic pivaloates to explore primitive dendrimer concept bicyclic compounds. Finally, we could obtain a series of diasteromeric compounds bearing two arms of 6-acylbicyclo[3,2,0] hept-6-ene groups in high yields.

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Section: Introductionmentioning

confidence: 65%

Synthesis of Primitive Dendrimer Systems Bearing Bicyclo[3,2,0]Hept‐6‐en‐6‐yl Groups via Unique Au‐catalyzed [2+2] Cyclization

Lee

Jillella

Kim

et al. 2018

Bulletin Korean Chem Soc

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“…(12.18)) [62]. Oh has reported the gold(I)-catalyzed rearrangement/cyclization of alkynyl propargyl acetates to form naphthyl ketone derivatives [63] and 2,3-bis(alkylidiene)cycloalkanones [64]. As an example of the former transformation, treatment of propargylic acetate 42 with a catalytic mixture of sodium tetrachloroaurate and triphenylphosphine in DCE at room temperature for 30 min led to isolation of naphthyl ketone 43 in 90% yield (Eq.…”

Section: Acyl Migration Followed By Nucleophilc Attackmentioning

confidence: 99%

Gold‐Catalyzed Addition of Oxygen Nucleophiles to CC Multiple Bonds

Widenhoefer

Song

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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The direct, catalytic addition of an oxygen nucleophile to a CÀC multiple bond represents an attractive approach to the formation of CÀO bonds from simple, readily available precursors. For this reason, there has been considerable interest in the identification of new and effective catalysts for the addition of oxygen nucleophiles to CÀC multiple bonds. One of the most significant developments in homogenous catalysis over the past 5-10 years has been the emergence of soluble gold complexes as catalysts for organic transformations [1]. Although a number of synthetically useful transformations have been developed, gold complexes have demonstrated particular utility as catalysts for the functionalization of CÀC multiple bonds with heteroatom nucleophiles, including oxygen nucleophiles such as water, carbinols, carbonyl compounds, and ethers. Early efforts in this area focused primarily on the application of simple gold(III) salts as catalysts, but interest has increasingly shifted toward the application of cationic gold(I) complexes supported by a phosphine or N-heterocyclic carbene ligands as catalysts for CÀO bond formation. These cationic gold(I) complexes are electrophilic, highly carbophilic compounds that are particularly suitable for p-activation catalysis. Herein we review the application of soluble gold(I) and gold(III) complexes as catalysts for the addition of oxygen nucleophiles to CÀC multiple bonds through 2008. This review is restricted to transformations that involve addition of an oxygen nucleophile to an electronically unactivated CÀC multiple bond catalyzed by a well-defined, soluble gold species.

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“…In a similar vein, cyclizations of diynes bearing propargyl carboxylates have been described to synthesize dienes 232 and pyrones (equation 90). 233 In the last case, a new cascade allows the intermolecular addition of electron-rich arenes.…”

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confidence: 97%

Gold in Homogeneous Catalysis

Jim��nez-N��ez¹,

Echavarren²

2005

Encyclopedia of Inorganic Chemistry

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Gold-catalyzed cyclizations of alkyne propargylic acetates to 2,3-bis(alkylidene)cycloalkanones and their related benzene derivatives

Abstract: We report a new and highly-convenient Au-catalyzed cyclization of alkyne propargylic acetates leading to 2,3-bis(alkylidene)cyclohexanones and their cycloadditions with a pendant dienophile.

Cited by 52 publications

References 23 publications

Synthesis of Primitive Dendrimer Systems Bearing Bicyclo[3,2,0]Hept‐6‐en‐6‐yl Groups via Unique Au‐catalyzed [2+2] Cyclization

Synthesis of Primitive Dendrimer Systems Bearing Bicyclo[3,2,0]Hept‐6‐en‐6‐yl Groups via Unique Au‐catalyzed [2+2] Cyclization

Gold‐Catalyzed Addition of Oxygen Nucleophiles to CC Multiple Bonds

Gold in Homogeneous Catalysis

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