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Volumn 12, Issue 8, 2010, Pages 1684-1687

Triquinanes: A "One-Pot" IMDA-tandem metathesis cascade strategy: Ring-closing metathesis (RCM) dominates norbornene ROM!

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EID: 77951184516     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100150f     Document Type: Article
Times cited : (28)

References (71)
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    • For the most recent synthesis, see
    • For the most recent synthesis, see
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    • Recent G3 ring strain energy calculations for norbornene (18.8 kcal/mol) norbornadiene (27.6 kcal/mol):, and references therein
    • Recent G3 ring strain energy calculations for norbornene (18.8 kcal/mol) norbornadiene (27.6 kcal/mol): Howell, J.; Goddard, J. D.; Tam, W. Tetrahedron 2009, 65, 4562 and references therein
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    • Howell, J.1    Goddard, J.D.2    Tam, W.3
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    • (a)Tandem norbornene metatheses
    • (a)Tandem norbornene metatheses
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    • Hetero-norbornenes
    • Hetero-norbornenes: Lui, Z.; Rainier, J. D. Org. Lett. 2005, 6, 131
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    • Microwave-assisted organic synthesis
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    • The glass encased Carboflon absorbs microwave energy, and the temperature and pressure are monitored by a fiber optic probe.
    • The glass encased Carboflon absorbs microwave energy, and the temperature and pressure are monitored by a fiber optic probe.
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    • This research also utilized the titanocene alkylidene complex to open their norbornene synthon.
    • Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855 This research also utilized the titanocene alkylidene complex to open their norbornene synthon.
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    • 2 was slowly added with vigorous stirring. The suspension was then transferred in a NMR tube and quickly introduced to the precooled (-18 °C) NMR probe.
    • 2 was slowly added with vigorous stirring. The suspension was then transferred in a NMR tube and quickly introduced to the precooled (-18 °C) NMR probe.
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    • The alkylidene ruthenium complex has been isolated (X-ray) from the reaction of a specially selected tricyclobutene with a full equivalent of catalyst
    • The alkylidene ruthenium complex has been isolated (X-ray) from the reaction of a specially selected tricyclobutene with a full equivalent of catalyst: Tallarico, J. L.; Bonitatebus, P. J., Jr.; M. Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 5157
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    • Tallarico, J.L.1    Bonitatebus Jr., P.J.2    Snapper M L, M.3
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    • Our result assumes the intermediates in the postulated pathways have sufficient lifetimes to be detected on the NMR time scale, although the back reactions may be fast.
    • Our result assumes the intermediates in the postulated pathways have sufficient lifetimes to be detected on the NMR time scale, although the back reactions may be fast.
  • 66
    • 77951155344 scopus 로고    scopus 로고
    • These results indicate the rate of the initial complexation-metallo- cycloaddition step determines the preferred pathway. This was confirmed by the detection of both competitive species. Consequently, the potential back reactions are not a complication.
    • These results indicate the rate of the initial complexation-metallo- cycloaddition step determines the preferred pathway. This was confirmed by the detection of both competitive species. Consequently, the potential back reactions are not a complication.
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    • Synthesis of 11
    • Synthesis of 11
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    • Crinipellins possess a rare angular tetraquinane skeleton for which only one total synthesis of (±)-crinipellin is known:;, A second allyl group in the cyclopentadienyl tether should facilitate the extension of our strategy to tetraquinane frameworks
    • Crinipellins possess a rare angular tetraquinane skeleton for which only one total synthesis of (±)-crinipellin is known: Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11 A second allyl group in the cyclopentadienyl tether should facilitate the extension of our strategy to tetraquinane frameworks
    • (1993) J. Org. Chem. , vol.58 , pp. 11
    • Piers, E.1    Renaud, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.