Highly Selective Skeletal Reorganization of 1,6- and 1,7-Enynes to 1-Vinylcycloalkenes Catalyzed by [RuCl2(CO)3]2

Chatani, Naoto; Morimoto, Tsumoru; Muto, Toyoshige; Murai, Shinji

doi:10.1021/ja00092a098

Cited by 250 publications

(137 citation statements)

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“…Fort he isolation of the products,the crude reaction mixture was flushed over ap lug of silica with ethyl acetate and concentrated. Am ixture of the products was obtained after which the yield was determined with 1 HNMR spectroscopy.T he spectral data of the products (6, [25] 7, [36] 8 [37] )c orresponded with those reported in the literature and were confirmed with COSY.F or the cyclization of enyne 9,n oi solation was performed but the spectral data of the products corresponded with those reported in the literature. [34] …”

Section: Standard Procedures For the Cyclization Of 3w Ith Activationsupporting

confidence: 75%

Gold Functionalized Platinum M₁₂L₂₄‐Nanospheres and Their Application in Cyclization Reactions

et al. 2016

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Nanospheres can be formed by combining 24 bispyridinyl building blocks with ap alladium or platinum precursor. Theses pheresc an be functionalized on the inside with ag old(I) chloride complex leading to ah igh local concentration of gold(I) complexes. Theh igh local concentration makes the neutral gold species an active catalyst. Furthermore,t he platinum-gold spheresc an be post-modified with as ilver(I) salt to form cationic gold(I) catalysts.T he platinum assemblies are demonstratedt ob es table in the presence of various substrates and as aresultseveral cyclization reactions have been carried out using these new spheres as catalysts.H igher conversions in a[ 4 + +2] cycloaddition are observed for the sphere catalyst comparedt ot he mono-nuclear analogues. Also the cyclization of 1,6-enynes can be facilitated by the confined gold catalyst and high activity is observed in the activation of allenes.F or the lactonization of alkynoic acids,adifferent selectivity is observed comparedt oastandard gold(I) complex, demonstrating that the high local concentration due to ac onfined space can induce other selectivity in catalysis.

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Section: Standard Procedures For the Cyclization Of 3w Ith Activationsupporting

confidence: 75%

Gold Functionalized Platinum M₁₂L₂₄‐Nanospheres and Their Application in Cyclization Reactions

et al. 2016

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“…The authors found that this interesting transformation could also be catalyzed by a series of other metal complexes, including 3 ] n , and ReCl(CO) 5 . This example illustrates the power of cycloisomerization processes to provide a rapid access to molecular complexity starting from readily accessible acyclic building blocks.…”

Section: Formation Of Bicycloa C H T U N G T R E N N U N G [410]hepmentioning

confidence: 99%

“…[5] Two years later, the same group reported that PtCl 2 efficiently catalyzed cycloisomerizations of 1,6-and 1,7-enynes to 1-vinylcycloalkenes (Scheme 3). [6] In a typical experiment described in this report, treatment of enyne 5 with 4 mol % of PtCl 2 in toluene at 80 8C under a nitrogen atmosphere afforded the cyclorearranged product 6 in 86 % yield.…”

Section: Introductionmentioning

confidence: 99%

Gold and Platinum Catalysis of Enyne Cycloisomerization

2006

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This account provides a comprehensive overview of the development of gold and platinum catalysis of the enyne cycloisomerization. The use of these soft, alkynophilic metals enables mild, chemoselective and efficient transformations of a variety of readily available acyclic enynes to a wide range of synthetically useful carbocyclic and heterocyclic products. The review is organized according to diverse structural types of enynes that undergo skeletal cycloisomerizations. The account begins with an overview of transformations of primarily 1,6-enynesheptenes. This section is followed by the discussion of cycloisomerizations of 1,5-enynes, which enable a rapid access to a range of other cyclic products, including bicycloA C H T U N G T R E N N U N G [3.1.0]hexenes, cyclohexadienes, heterobicycloalkenes, methylenecyclopentenes, naphthalenes and methyleneindenes. In addition, the [3,3] rearrangement of 1,5-enynes provides efficient access to the corresponding allenes. The account concludes with an overview of the most recent studies on gold-and platinum-catalyzed cycloisomerizations of 1,4-and 1,3-enynes. Due to the rapidly increasing interest in this area during the past three to five years, we believe that this review provides a timely and comprehensive discussion of the development gold-and platinum-catalyzed cycloisomerization starting from the initial pioneering investigations to the latest advances in the field. A significant emphasis is placed on the mechanistic discussion of the observed manifolds of skeletal reorganizations.

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“…[24,25] In 1994, Murai and Chatani reported skeletal reorganization of 1,6-enynes using [RuCl 2 (CO) 3 ] 2 as a catalyst. [26] Then they found that GaCl 3 was effective for skeletal reorganization. [27] Using these various enyne metatheses, complicated natural products have been synthesized via a novel route and the synthetic routes are completely different from that described in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Natural Products and Related Compounds using Enyne Metathesis

Mori

2007

Adv Synth Catal

148

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Since the molybdenum and ruthenium carbene complexes 1a and 1b were discovered by Schrock and Grubbs in 1990 and 1992, synthetic organic chemistry has progressed with the use of these complexes as the catalyst for olefin metathesis. It was found that the ruthenium carbene complex was also effective for enyne metathesis, which occurs between an alkene and an alkyne. Intramolecular enyne metathesis gives various cyclic compounds having a 1,3-diene moiety and cross-metathesis of an alkene with an alkyne is a useful method for the synthesis of a compound having a diene moiety. Furthermore, dienyne metathesis, ROM of cycloalkenynes or tandem reactions of enyne metathesis have been developed. Using these various enyne metatheses, complicated natural products have been synthesized via novel routes. The syntheses of natural products and related compounds using enyne metathesis are described.

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Highly Selective Skeletal Reorganization of 1,6- and 1,7-Enynes to 1-Vinylcycloalkenes Catalyzed by [RuCl2(CO)3]2

Cited by 250 publications

References 0 publications

Gold Functionalized Platinum M₁₂L₂₄‐Nanospheres and Their Application in Cyclization Reactions

Gold Functionalized Platinum M₁₂L₂₄‐Nanospheres and Their Application in Cyclization Reactions

Gold and Platinum Catalysis of Enyne Cycloisomerization

Synthesis of Natural Products and Related Compounds using Enyne Metathesis

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Highly Selective Skeletal Reorganization of 1,6- and 1,7-Enynes to 1-Vinylcycloalkenes Catalyzed by [RuCl2(CO)3]2

Cited by 250 publications

References 0 publications

Gold Functionalized Platinum M12L24‐Nanospheres and Their Application in Cyclization Reactions

Gold Functionalized Platinum M12L24‐Nanospheres and Their Application in Cyclization Reactions

Gold and Platinum Catalysis of Enyne Cycloisomerization

Synthesis of Natural Products and Related Compounds using Enyne Metathesis

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Gold Functionalized Platinum M₁₂L₂₄‐Nanospheres and Their Application in Cyclization Reactions

Gold Functionalized Platinum M₁₂L₂₄‐Nanospheres and Their Application in Cyclization Reactions