Ruthenium-Catalyzed [2+2+2] Bis-Homo-Diels–Alder Cycloadditions of 1,5-Cyclooctadiene with Alkynyl Phosphonates

Petko, Dina; Pounder, Austin; Tam, William

doi:10.1055/s-0039-1690612

Cited by 5 publications

(2 citation statements)

References 20 publications

(30 reference statements)

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“…In 2019, Tam and co-workers reported the Ru-catalyzed [2+2+2] bis-homo-Diels-Alder cycloaddition of cycloocta-1,5-diene with alkynylphosphonates to access tricyclo[4.2.2.0 2,5 ]dec-7-ene tricyclic compounds (Scheme 50). 111 In the presence of [Cp*RuCl(cod)] or [CpRu(CH 3 CN) 3 ]PF 6 , the reaction afforded the desired cycloadducts in 46-97% yield and was tolerant to steric bulk on both the phosphonate and the alkynyl moieties.…”

Section: Scheme 49mentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition.1 Introduction2 Formation of Carbocycles2.1 Intermolecular Reactions2.1.1 Cyclotrimerization of Alkynes2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions3 Formation of Heterocycles3.1 Cycloaddition of Alkynes with Nitriles3.2 Cycloaddition of 1,6-Diynes with Cyanamides3.3 Cycloaddition of 1,6-Diynes with Selenocyanates3.4 Cycloaddition of Imines with Allenes or Alkenes3.5 Cycloaddition of (Thio)Cyanates and Isocyanates3.6 Cycloaddition of 1,3,5-Triazines with Allenes3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions4 Conclusion

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Section: Scheme 49mentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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“…176 In 2019, Tam further extended the scope of the reaction to include acetylenic phosphonates as 2π-components (Scheme 33). 177 In 2004, Tenaglia reported a ruthenium-catalyzed homo-Diels−Alder reaction of internal alkynes with norbornadiene to form 8,9-disubstituted deltacyclenes (Scheme 34). 178 The ruthenium catalyst [(nbd)RuCl 2 (PPh 3 ) 2 ] was found to provide optimal yields of cycloadduct.…”

Section: [2+2+2] Cycloadditions Of Cod and Nbd As 2 2πmentioning

confidence: 99%

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Doerksen

Hodík

et al. 2021

Chem. Rev.

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Ruthenium-catalyzed cycloadditions to form five-, six-, and seven-membered rings are summarized, including applications in natural product total synthesis. Content is organized by ring size and reaction type. Coverage is limited to processes that involve formation of at least one C–C bond. Processes that are stoichiometric in ruthenium or exploit ruthenium as a Lewis acid (without intervention of organometallic intermediates), ring formations that occur through dehydrogenative condensation-reduction, σ-bond activation-initiated annulations that do not result in net reduction of bond multiplicity, and photochemically promoted ruthenium-catalyzed cycloadditions are not covered.

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Unusual In‐Situ Preorganization and Postoxidation Steps Observed in Diels‐Alder Reactions of Styrylcyclohexene Dienes

et al. 2021

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Unusual products were obtained from cycloadditions reactions of two series of styrylcyclohexene dienes with dienophiles maleic anhydride and N‐phenylmaleimide. Experimental studies revealed that various dienes 3 underwent an initial in‐situ dehydration/double bond rearrangement prior to cycloaddition with maleic anhydride to give products 5 in 78–88 % yields. Alternatively, the cycloadducts of the reactions of 4 with N‐phenylmaleimide were hydoxylated stereoselectively in the same pot to give products 7, along with the usual adducts 6 in 83–89 % yields. Further, the reactions of the diene 4 with the dienophile dimethyl acetylenedicarboxylate were also studied, leading to the formation of the respective adducts 10 in 72–81 % yields. The stereochemistry of the new products was assigned based on their spectroscopic data and, in some cases, with X‐ray crystallography experiments.

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Ruthenium-Catalyzed [2+2+2] Bis-Homo-Diels–Alder Cycloadditions of 1,5-Cyclooctadiene with Alkynyl Phosphonates

Cited by 5 publications

References 20 publications

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Unusual In‐Situ Preorganization and Postoxidation Steps Observed in Diels‐Alder Reactions of Styrylcyclohexene Dienes

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