Rhodium(I)-Catalyzed [2+2], [2+2+2], and [2+2+2+2] Cycloadditions of Dienes or Alkynes with a Bis-ene

Wender, Paul A.; Croatt, Mitchell P.; Kühn, Björn

doi:10.1021/om9007373

Cited by 19 publications

(6 citation statements)

References 32 publications

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“…One of the few examples of utilising Rh(I)-arene complexes for cycloaddition reactions was provided by Wender et al 68 They used [Rh(COD)(naphthalene)]SbF 6 for the coupling of dienes or alkynes with alkene compounds in [2+2], [2+2+2] and [2+2+2+2] cycloadditions. It was found that the carbon monoxide can play an important role in switching the reaction between the different reaction types.…”

Section: Rhodium(i)-complexes As Catalystsmentioning

confidence: 99%

Preparation and synthetic applications of alkene complexes of group 9 transition metals in [2+2+2] cycloaddition reactions

2011

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The [2+2+2] cycloaddition reaction has become an invaluable tool for the synthetic chemistry in recent years, due to the increase of complexity of the accessed target molecules by this methodology. Over several decades, the members of group 9 of the periodic table have contributed significantly to the development and understanding of this particular cycloaddition reaction. On the other hand, catalyst complexes containing alkenes as ligands are widely used today as either catalysts or as precursor molecules for the facile generation of catalytically active metal species. In this tutorial review we want to describe the catalytically relevant chemistry of group 9 metal-alkene complexes and compile some recent applications in [2+2+2] cycloaddition reactions.

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Section: Rhodium(i)-complexes As Catalystsmentioning

confidence: 99%

Preparation and synthetic applications of alkene complexes of group 9 transition metals in [2+2+2] cycloaddition reactions

2011

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“…Recently, Wender and co-workers reported the Rh-catalyzed [2+2+2] cycloaddition of 25 with dienes to afford the corresponding tetracyclic products 147 (Scheme 35) [42]. These authors proposed a mechanism involving oxidative cyclization of 25 to afford a metallotetracyclic intermediate 148.…”

Section: Metal-catalyzed/mediated Reactions Of Cyclooctatetraene Valementioning

confidence: 99%

Recent Applications of the Simple Hydrocarbon Cyclooctatetrene as a Starting Material for Complex Molecule Synthesis

Glaeske¹,

Donaldson²

2012

MROC

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Cyclooctatetraene [COT], a simple non-aromatic cyclic polyene, is capable of undergoing a variety of oxidation and cycloaddition reactions to afford polycyclic structures. In addition, complexation of COT or the cycloaddition products with transition metals facilitates bond formation. Recent developments in the reactivity of COT and application to the synthesis of naturally occurring and non-naturally occurring compounds is reviewed.

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“…To rapidly implement molecular complexity from readily available simple starting materials, transition metal-catalyzed carbocyclization and cycloaddition reactions are recognized as synthetically very important processes. − Considerable advances have been made recently in the development of higher order cycloaddition reactions such as [2+2+2+1], − [3+3+1], [2+2+2+2], − [4+2+2], − [5+2+1], − and [5+1+2+1] processes. Various polycyclization reactions have been employed for the construction of natural and unnatural fused-ring systems that can be further elaborated into specific targets.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Colchicinoids and Allocolchicinoids through Rh(I)-Catalyzed [2+2+2+1] and [2+2+2] Cycloadditions of o-Phenylenetriynes with and without CO

et al. 2018

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The nonbenzenoid aromatics, tropones and tropolones, are found in various natural products such as colchicine and hinokitol, which possess significant biological activities. The traditional methods to construct the tropone skeletons include oxidation of cycloheptatriene and [4+3] cycloadditions. In addition, the total synthesis of colchicine and its analogues requires laborious organic transformations in the formations of 6-7-7 fused-ring systems. Transition metal-catalyzed carbocyclization and cycloaddition reactions have proven to be among the most efficient methods for constructing complex polycyclic systems. On the basis of our recent discovery of the Rh-catalyzed carbonylative [2+2+2+1] cycloaddition of triynes to the formation of a fused tropone system, we report here the application of this methodology to the one-step formation of the 6-7-7-5 fused tetracyclic scaffold of colchicinoids based on the [2+2+2+1] cycloaddition of o-phenylenetriynes with CO. In addition, the one-step formation of allocolchicinoids bearing the 6-7-6-5 fused tetracyclic system through the Rh-catalyzed [2+2+2] cycloaddition of o-phenylenetriynes is also described.

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Rhodium(I)-Catalyzed [2+2], [2+2+2], and [2+2+2+2] Cycloadditions of Dienes or Alkynes with a Bis-ene

Cited by 19 publications

References 32 publications

Preparation and synthetic applications of alkene complexes of group 9 transition metals in [2+2+2] cycloaddition reactions

Preparation and synthetic applications of alkene complexes of group 9 transition metals in [2+2+2] cycloaddition reactions

Recent Applications of the Simple Hydrocarbon Cyclooctatetrene as a Starting Material for Complex Molecule Synthesis

Synthesis of Colchicinoids and Allocolchicinoids through Rh(I)-Catalyzed [2+2+2+1] and [2+2+2] Cycloadditions of o-Phenylenetriynes with and without CO

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