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Volumn 13, Issue 6, 2011, Pages 1490-1493

Asymmetric synthesis of tertiary and quaternary allyl- and crotylsilanes via the borylation of lithiated carbamates

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EID: 79952578940     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200177f     Document Type: Article
Times cited : (73)

References (43)
  • 14
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    • 2, couples with vinyl halides to give allylsilanes [see:, ] the more substituted 1,1-silaboronic acid pinacol esters do not [see: J. Am. Chem. Soc. 2010, 132, 11033-11035.] and so this strategy cannot be used to make tertiary or quaternary allylsilanes. Endo et al. did report the successful coupling of substituted 1,1-bisboronic acid pinacol esters. Apart from this and other isolated cases, secondary boronic acids/pinacol esters do not normally undergo efficient Suzuki-Miyaura cross-coupling For a review, see: Chem. Commun. 2009, 6704-6716
    • 2, couples with vinyl halides to give allylsilanes [see: Zou, G.; Reddy, Y. K.; Falck, J. R. Tetrahedron Lett. 2001, 42, 7213-7215 ] the more substituted 1,1-silaboronic acid pinacol esters do not [see: Endo, K.; Ohkubo, T.; Hirokami, M.; Shibata, T. J. Am. Chem. Soc. 2010, 132, 11033-11035.] and so this strategy cannot be used to make tertiary or quaternary allylsilanes. Endo et al. did report the successful coupling of substituted 1,1-bisboronic acid pinacol esters. Apart from this and other isolated cases, secondary boronic acids/pinacol esters do not normally undergo efficient Suzuki-Miyaura cross-coupling For a review, see: Crudden, C. M.; Glasspoole, B. W.; Lata, C. J. Chem. Commun. 2009, 6704-6716
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7213-7215
    • Zou, G.1    Reddy, Y.K.2    Falck, J.R.3    Endo, K.4    Ohkubo, T.5    Hirokami, M.6    Shibata, T.7    Crudden, C.M.8    Glasspoole, B.W.9    Lata, C.J.10
  • 17
    • 0001613954 scopus 로고
    • Hartley F.R. Ed.; Wiley, and references therein.
    • Matteson, D. S. In The Chemistry of the Metal-carbon Bond, Hartley, F. R., Ed.; Wiley: 1987; Vol. 4, pp 307 - 499 and references therein.
    • (1987) The Chemistry of the Metal-carbon Bond , vol.4 , pp. 307-499
    • Matteson, D.S.1
  • 25
    • 8744278889 scopus 로고    scopus 로고
    • Our attempts to effect the lithiation-borylation reaction, shown in Scheme 1, only gave racemic allylsilane 4 (R = Ph) even when the reaction was conducted at -100 °C. The configurational instability of silyl-substituted lithiated carbamates has been noted before
    • Our attempts to effect the lithiation-borylation reaction, shown in Scheme 1, only gave racemic allylsilane 4 (R = Ph) even when the reaction was conducted at -100 °C. The configurational instability of silyl-substituted lithiated carbamates has been noted before: Simov, B. P.; Rohn, A.; Brecker, L.; Giester, G.; Hammerschmidt, F. Synthesis 2004, 16, 2704-2710
    • (2004) Synthesis , vol.16 , pp. 2704-2710
    • Simov, B.P.1    Rohn, A.2    Brecker, L.3    Giester, G.4    Hammerschmidt, F.5
  • 31
    • 0000347750 scopus 로고
    • The silaboration has been pioneered by Buynak using ethyl diazoacetate as the carbenoid: Buynak, J. D.; Geng, B. Organometallics 1995, 14, 3112-3115
    • (1995) Organometallics , vol.14 , pp. 3112-3115
    • Buynak, J.D.1    Geng, B.2
  • 34
    • 0001342971 scopus 로고
    • Preparation of vinyllithium:, Preparation of propenyllithium: Tetrahedron Lett. 1976, 52, 4839-4842
    • Preparation of vinyllithium: Gassman, P. G.; Valcho, J. J.; Proehl, G. S.; Cooper, C. F. J. Am. Chem. Soc. 1980, 102, 6519-6526 Preparation of propenyllithium: Neumann, H.; Seebach, D. Tetrahedron Lett. 1976, 52, 4839-4842
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 6519-6526
    • Gassman, P.G.1    Valcho, J.J.2    Proehl, G.S.3    Cooper, C.F.4    Neumann, H.5    Seebach, D.6
  • 42
    • 79952595152 scopus 로고    scopus 로고
    • CCDC 800290 contains the supplementary crystallographic data for the alcohol obtained from allylsilane 19b by hydroboration/oxidation. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 800290 contains the supplementary crystallographic data for the alcohol obtained from allylsilane 19b by hydroboration/oxidation. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.