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Volumn 11, Issue 13, 2009, Pages 2880-2883

Kinetic resolution of racemic 1 -alkyl-2-methylenecyclopropanes via palladium-catalyzed silaborative C-C cleavage

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EID: 67649511756     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900829c     Document Type: Article
Times cited : (40)

References (40)
  • 11
    • 0035953045 scopus 로고    scopus 로고
    • Reviews on kinetic resolution, see: a
    • Reviews on kinetic resolution, see: (a) Kagan, H. B. Tetrahedron 2001, 57, 2449.
    • (2001) Tetrahedron , vol.57 , pp. 2449
    • Kagan, H.B.1
  • 16
    • 0042192126 scopus 로고    scopus 로고
    • For related studies on asymmetric silaboration, see: (a) Suginome, M.; Ohmura, T.; Miyake, Y.; Mitani, S.; Ito, Y.; Murakami, M. J. Am. Chem. Soc. 2003, 125, 11.174.
    • For related studies on asymmetric silaboration, see: (a) Suginome, M.; Ohmura, T.; Miyake, Y.; Mitani, S.; Ito, Y.; Murakami, M. J. Am. Chem. Soc. 2003, 125, 11.174.
  • 18
    • 33750350817 scopus 로고    scopus 로고
    • For recent reviews on bismetallation of unsaturated hydrocarbons, see
    • Ohmura, T.; Taniguchi, H.; Suginome, M. J. Am. Chem. Soc. 2006,128, 13682. For recent reviews on bismetallation of unsaturated hydrocarbons, see:
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 13682
    • Ohmura, T.1    Taniguchi, H.2    Suginome, M.3
  • 20
    • 84906432766 scopus 로고    scopus 로고
    • Suginome, M.; Matsuda, T.: Ohmura. T.; Seki, A.; Murakami, M. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.; Ojima, I., Ed.; Elsevier: Oxford, 2007; 10, p 725.
    • (e) Suginome, M.; Matsuda, T.: Ohmura. T.; Seki, A.; Murakami, M. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.; Ojima, I., Vol. Ed.; Elsevier: Oxford, 2007; Vol. 10, p 725.
  • 24
    • 67649540107 scopus 로고    scopus 로고
    • In this paper, we used the term parallel kinetic resolution for the reaction in which each enantiomer of racemic substrate was separately converted into constitutional isomers
    • In this paper, we used the term "parallel kinetic resolution" for the reaction in which each enantiomer of racemic substrate was separately converted into constitutional isomers,
  • 25
    • 67649521719 scopus 로고    scopus 로고
    • Examples of parallel kinetic resolution using chiral transition-metal catalyst : (a) Hayashi, T.; Yamamoto, A.; Ito, Y. Chem. Lett. 1987, 177.
    • Examples of parallel kinetic resolution using chiral transition-metal catalyst : (a) Hayashi, T.; Yamamoto, A.; Ito, Y. Chem. Lett. 1987, 177.
  • 37
    • 34447117685 scopus 로고    scopus 로고
    • The kinetic resolution system, in which secondary selection is operating synergistically has been reported recently in the ring opening of unsymmetrically substituted cis-epoxides: Arai, K.; Lucarini, S.; Salter, M. M.; Ohta, K.; Yamashita, Y.; Kobayashi, S. J. Am Chem. Soc. 2007, 129, 8103.
    • The kinetic resolution system, in which secondary selection is operating synergistically has been reported recently in the ring opening of unsymmetrically substituted cis-epoxides: Arai, K.; Lucarini, S.; Salter, M. M.; Ohta, K.; Yamashita, Y.; Kobayashi, S. J. Am Chem. Soc. 2007, 129, 8103.
  • 38
    • 67649543405 scopus 로고    scopus 로고
    • The reactions of sterically demanding 2 (R = Ph and cyclohexyl) took place slowly under the same reaction conditions (63% conversion after 48 h, R = cyclohexyl), although we have not been able to find conditions for HPLC analysis with, chiral stationary phase column.
    • The reactions of sterically demanding 2 (R = Ph and cyclohexyl) took place slowly under the same reaction conditions (63% conversion after 48 h, R = cyclohexyl), although we have not been able to find conditions for HPLC analysis with, chiral stationary phase column.
  • 39
    • 33744795339 scopus 로고    scopus 로고
    • For a review on β-silyl carbonyl compounds, see:, Fleming, I, Ed, Thieme: Stuttgart
    • For a review on β-silyl carbonyl compounds, see: Fleming, I. In Science of Synthesis; Fleming, I., Ed.; Thieme: Stuttgart, 2002; Vol. 4, p 927.
    • (2002) Science of Synthesis , vol.4 , pp. 927
    • Fleming, I.1
  • 40
    • 67649559049 scopus 로고    scopus 로고
    • 2 (5 mol %) with 5 N NaOH (3 equiv) resulted in the formation of the corresponding coupling products in 70% total yield after 6 h.
    • 2 (5 mol %) with 5 N NaOH (3 equiv) resulted in the formation of the corresponding coupling products in 70% total yield after 6 h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.