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Volumn 78, Issue 8, 2005, Pages 1528-1533

Addition/ring-opening reaction of organoboronic acids to cyclobutanones catalyzed by rhodium(I)/P(t-Bu)3 complex

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; KETONES; RHODIUM COMPOUNDS;

EID: 23844547924     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.78.1528     Document Type: Article
Times cited : (36)

References (53)
  • 29
    • 0002583629 scopus 로고    scopus 로고
    • Activation of unreactive bond and organic synthesis
    • ed by S. Murai, Springer, Berlin
    • b) M. Murakami and Y. Ito, "Activation of Unreactive Bond and Organic Synthesis," in "Topics in Organometallic Chemistry," ed by S. Murai, Springer, Berlin (1999), Vol. 3, p. 97.
    • (1999) Topics in Organometallic Chemistry , vol.3 , pp. 97
    • Murakami, M.1    Ito, Y.2
  • 42
    • 33645345722 scopus 로고    scopus 로고
    • note
    • Tertiary cyclobutanols 4aa and 4ab were synthesized independently by the reaction of 1a with the corresponding Grignard reagents and used as a diastereomeric mixture (4aa: cis:trans = 96:4; 4ab: cis:trans = 74:26).
  • 43
    • 33645345998 scopus 로고    scopus 로고
    • note
    • 1H NMR; however, the relative stereochemistries were not determined.
  • 44
    • 0037181029 scopus 로고    scopus 로고
    • Insertion of aldehyde into rhodium-aryl bond was observed by Hartwig. C. Krug and J. F. Hartwig, J. Am. Chem. Soc., 124, 1674 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1674
    • Krug, C.1    Hartwig, J.F.2
  • 45
    • 1342302388 scopus 로고    scopus 로고
    • For a review on β-carbon elimination from Pd(II) cyclobutanolate, see: T. Nishimura and S. Uemura, Synlett, 2004, 201.
    • Synlett , vol.2004 , pp. 201
    • Nishimura, T.1    Uemura, S.2
  • 46
    • 0037433553 scopus 로고    scopus 로고
    • For transition metal-hydride elimination followed by re-addition with the opposite regiochemistry, see: a) K. Yoshida and T. Hayashi, J. Am. Chem. Soc., 125, 2872 (2003).
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2872
    • Yoshida, K.1    Hayashi, T.2
  • 49
    • 33645344381 scopus 로고    scopus 로고
    • note
    • Ring-opened ketone was also isolated in 2%.
  • 50
    • 0037509951 scopus 로고    scopus 로고
    • For synthetic applications of cyclobutane derivatives, see: J. C. Namyslo and D. E. Kaufmann, Chem. Rev., 103, 1485 (2003).
    • (2003) Chem. Rev. , vol.103 , pp. 1485
    • Namyslo, J.C.1    Kaufmann, D.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.