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Volumn 132, Issue 4, 2010, Pages 1226-1227

Copper(I)-catalyzed asymmetric monoborylation of 1,3-dienes: Synthesis of enantioenriched cyclic homoallyl- and allylboronates

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLBORONATES; CHEMICAL EQUATIONS; CYCLOHEXADIENES; CYCLOPENTADIENES; OPTICALLY ACTIVE; REACTION CONDITIONS;

EID: 77950453311     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja909640b     Document Type: Article
Times cited : (194)

References (29)
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    • For examples of asymmetric catalytic hydroboration, see: (a) Hayashi, T, Matsumoto, Y, Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426-3428
    • For examples of asymmetric catalytic hydroboration, see: (a) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426-3428.
  • 11
    • 33947473053 scopus 로고    scopus 로고
    • For examples of asymmetric stoichiometric hydroboration, see: (a) Brown, H. C, Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486-487
    • For examples of asymmetric stoichiometric hydroboration, see: (a) Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486-487.
  • 14
    • 0000231794 scopus 로고
    • For nonasymmetric metal-catalyzed 1,4-hydroboration of 1,3-dienes, see: a
    • For nonasymmetric metal-catalyzed 1,4-hydroboration of 1,3-dienes, see: (a) Satoh, M.; Nomoto, Y.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1989, 30, 3789-3792.
    • (1989) Tetrahedron Lett , vol.30 , pp. 3789-3792
    • Satoh, M.1    Nomoto, Y.2    Miyaura, N.3    Suzuki, A.4
  • 16
    • 67649964459 scopus 로고    scopus 로고
    • For metal-catalyzed asymmetric 1,4-diboration of 1,3-diene, see
    • For metal-catalyzed asymmetric 1,4-diboration of 1,3-diene, see: Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134-9135.
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 9134-9135
    • Burks, H.E.1    Kliman, L.T.2    Morken, J.P.3
  • 17
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    • All enantioenriched homoallyl- and allylboronates prepared in this paper, including very simple ones 3a, 3j, 3k, 4j, and 4k, have not been previously reported
    • All enantioenriched homoallyl- and allylboronates prepared in this paper, including very simple ones (3a, 3j, 3k, 4j, and 4k), have not been previously reported.
  • 18
    • 36849074311 scopus 로고    scopus 로고
    • For our results on asymmetric copper(I)-catalyzed reactions with diboron, see: (a) Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. J. Am. Chem. Soc. 2007, 129, 14856-14857.
    • For our results on asymmetric copper(I)-catalyzed reactions with diboron, see: (a) Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. J. Am. Chem. Soc. 2007, 129, 14856-14857.
  • 25
    • 37049066644 scopus 로고    scopus 로고
    • It was reported that the regioselectivity in hydroboration of 1,3-dienes with Ipc2BH is substrate dependent. 1,3-Cyclopentadiene gave the homoallylborane; 1,3-cyclohexa-, hepta-, and nonadiene gave the allylboranes. See: (a) Brown, H. C.; Bhat, K. S.; Jadhav, P. K. J. Chem. Soc., Perkin Trans. 1 1991, 2633-2638.
    • It was reported that the regioselectivity in hydroboration of 1,3-dienes with Ipc2BH is substrate dependent. 1,3-Cyclopentadiene gave the homoallylborane; 1,3-cyclohexa-, hepta-, and nonadiene gave the allylboranes. See: (a) Brown, H. C.; Bhat, K. S.; Jadhav, P. K. J. Chem. Soc., Perkin Trans. 1 1991, 2633-2638.
  • 27
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    • For studies on copper(I)-catalyzed reaction of activated alkenes, see: (a) Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. Organometallics 2006, 25, 2405-2408.
    • For studies on copper(I)-catalyzed reaction of activated alkenes, see: (a) Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. Organometallics 2006, 25, 2405-2408.
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    • Dang, L.; Zhao, H.; Lin, Z.; Marder, T. B. Organometallics 2007, 26, 2824-2832, See also ref 2d.
    • (b) Dang, L.; Zhao, H.; Lin, Z.; Marder, T. B. Organometallics 2007, 26, 2824-2832, See also ref 2d.
  • 29
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    • For related mechanistic studies on the reaction of allylcopper(I) species, see: Liepins, V.; Bäckvall, J. E. Eur. J. Org. Chem. 2002, 3527-3535.
    • For related mechanistic studies on the reaction of allylcopper(I) species, see: Liepins, V.; Bäckvall, J. E. Eur. J. Org. Chem. 2002, 3527-3535.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.