Synthesis of Small and Large Fused Bicyclic Compounds by Tandem Dienyne Ring-Closing Metathesis

Park, Hyeon; Hong, You‐lee; Kim, Yongjoo B.; Choi, Tae‐Lim

doi:10.1021/ol101233k

Cited by 23 publications

(8 citation statements)

References 41 publications

(17 reference statements)

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“…Then, N-phenylmaleimide was added to the reaction mixture to form the Diels-Alder adducts 211 as single isomers in good yields (Scheme 53). Recently, Choi and co-workers [90] described a tandem dienyne RCM of 212 to generate macrocyclic 1,3-diene 213 followed by a Diels-Alder reaction. In contrast to s-trans-1,3-dienes embedded in two small fused bicycles, the macrocyclic 1,3-diene 213 can assume an s-cis conformation, which allows its Diels-Alder reaction with maleic anhydride to give 214.…”

Section: Tandem Enyne Metathesis/diels-alder Reactionmentioning

confidence: 99%

Enyne‐Metathesis‐Based Tandem Processes

Lee

2011

Eur J Org Chem

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Section: Tandem Enyne Metathesis/diels-alder Reactionmentioning

confidence: 99%

Enyne‐Metathesis‐Based Tandem Processes

Lee

2011

Eur J Org Chem

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“…13 Recently, we demonstrated a versatile tandem reaction combining macrocyclisation and dienyne RCM to give bicyclic compounds comprising small and large rings. 14 Herein, we report the details of our preliminary results of the tandem RCM reaction. The resulting fused bicycles containing macrocycles proved to be good dienes for the Diels-Alder reaction, producing fused multicyclic compounds containing macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of fused multicyclic compounds containing macrocycles by dienyne ring-closing metathesis and Diels–Alder reactions

Park

Choi

2011

Org. Biomol. Chem.

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Fused bicyclic compounds comprising small and large rings were synthesised by dienyne ring-closing metathesis (RCM) using Grubbs' catalyst. By taking advantage of faster small ring cyclisation compared with macrocyclisation, single isomers were obtained rather than mixtures of two isomers with different ring sizes. Using this process, various fused bicyclic compounds comprising small rings (5-7- membered) and large rings (14-17- membered) were obtained. By increasing reaction temperature and catalyst loading, the product conversion was improved in a predicted manner. This method produced E-olefins on the macrocycles with high selectivity. Also, the selectivity issues of tandem RCM for the synthesis of fused bicyclic compounds comprising small and medium rings were investigated. Lastly, the prepared bicyclic compounds with small and large rings contained 1, 3-dienes that underwent a further modification reaction, such as Diels-Alder, to produce more complex compounds. These Diels-Alder reactions produced tri- and tetracyclic compounds containing a macrocycle with single diastereomers, suggesting that the methodology demonstrated here could be a powerful tool for rapid preparation of highly complex molecules.

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“…Sequence-selective cascade metathesis reactions have mainly been used for the synthesis of organic molecules and functional catalysts. − However, few of such reactions have also been explored in polymer synthesis. Choi and co-workers reported an elegant strategy allowing polymerization of alkyne and cyclohexene functional groups present within a single monomer in an alternating manner via a tandem ring-opening/ring-closing metathesis (RO/RCM) reaction. − There, the alkyne is an example of a slowly homopropagating monomer, and cyclohexene is an example of a monomer with very low ring strain (1.6 kcal/mol) …”

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confidence: 99%

Cascade Ring-Opening/Ring-Closing Metathesis Polymerization of a Monomer Containing a Norbornene and a Cyclohexene Ring

Yasir

Kilbinger

2021

ACS Macro Lett.

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Norbornene is polymerized extremely fast when reacted with Grubbs' first (G1) or third generation catalyst (G3) because of its very high ring strain energy. Cyclohexene, on the other hand, cannot be polymerized using G1 or G3 due to its very low ring strain energy. Subsequently, the sequence selective polymerization of these two monomers is extremely challenging. A sequence selective cascade ring opening/ring closing metathesis polymerization of the monomer M containing both, the norbornene and the cyclohexene ring using G1 or G3 is reported. The polymer structure was analyzed by 1 H NMR, 1 H-1 H COSY and 1 H-1 H ROESY spectroscopy and MALDI-ToF mass spectrometry. Polymers with moderate molecular weight dispersities and good molecular weight control were achieved by varying the ratio between monomer M and G1.

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Synthesis of Small and Large Fused Bicyclic Compounds by Tandem Dienyne Ring-Closing Metathesis

Cited by 23 publications

References 41 publications

Enyne‐Metathesis‐Based Tandem Processes

Enyne‐Metathesis‐Based Tandem Processes

Synthesis of fused multicyclic compounds containing macrocycles by dienyne ring-closing metathesis and Diels–Alder reactions

Cascade Ring-Opening/Ring-Closing Metathesis Polymerization of a Monomer Containing a Norbornene and a Cyclohexene Ring

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