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Volumn 33, Issue 4, 2004, Pages 404-405

Regioselective formation of optically active cycloheptatrienes by chiral tethered büchner reaction

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; HEPTANE DERIVATIVE; PENTANE; PHENYL GROUP; RHODIUM DERIVATIVE;

EID: 3142670026     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.404     Document Type: Article
Times cited : (10)

References (18)
  • 1
    • 2142666603 scopus 로고    scopus 로고
    • ed. by S. G. Pandalai, Transworld Research Network, Trivandrum
    • T. Sugimura, in "Recent Research Developments in Organic Chemistry," ed. by S. G. Pandalai, Transworld Research Network, Trivandrum (1998), Vol. 2, pp 47-53.
    • (1998) Recent Research Developments in Organic Chemistry , vol.2 , pp. 47-53
    • Sugimura, T.1
  • 3
    • 0000769223 scopus 로고
    • ed. by B. M. Trost, Pergamon, Oxford
    • For Büchner reaction, see: H. M. L. Davies, in "Comprehensive Organic Synthesis," ed. by B. M. Trost, Pergamon, Oxford (1991), Vol. 4, pp 1031-1067; G. Mass, in "Topics in Current Chemistry," Springer-Verlag, Berlin (1987), Vol. 137, pp 75-253; M. P. Doyle, M. A. McKervey, and T. Ye, "Modern Catalytic Methods for Organic Synthesis with Diazo Compounds," Wiley, New York (1998), Chap. 6.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1031-1067
    • Davies, H.M.L.1
  • 4
    • 0001871942 scopus 로고
    • Springer-Verlag, Berlin
    • For Büchner reaction, see: H. M. L. Davies, in "Comprehensive Organic Synthesis," ed. by B. M. Trost, Pergamon, Oxford (1991), Vol. 4, pp 1031-1067; G. Mass, in "Topics in Current Chemistry," Springer-Verlag, Berlin (1987), Vol. 137, pp 75-253; M. P. Doyle, M. A. McKervey, and T. Ye, "Modern Catalytic Methods for Organic Synthesis with Diazo Compounds," Wiley, New York (1998), Chap. 6.
    • (1987) Topics in Current Chemistry , vol.137 , pp. 75-253
    • Mass, G.1
  • 5
    • 0003394220 scopus 로고    scopus 로고
    • Wiley, New York Chap. 6
    • For Büchner reaction, see: H. M. L. Davies, in "Comprehensive Organic Synthesis," ed. by B. M. Trost, Pergamon, Oxford (1991), Vol. 4, pp 1031-1067; G. Mass, in "Topics in Current Chemistry," Springer-Verlag, Berlin (1987), Vol. 137, pp 75-253; M. P. Doyle, M. A. McKervey, and T. Ye, "Modern Catalytic Methods for Organic Synthesis with Diazo Compounds," Wiley, New York (1998), Chap. 6.
    • (1998) Modern Catalytic Methods for Organic Synthesis with Diazo Compounds
    • Doyle, M.P.1    McKervey, M.A.2    Ye, T.3
  • 11
    • 3142782193 scopus 로고    scopus 로고
    • note
    • 2 as follows: a) Mitsunobu reaction of (2R,4R)-2,4-pentanediol with 3-chlorophenol or 3-methoxy-carbonylphenol (79.6 and 86.5% yields, respectively), b) formation of acetoacetate ester with diketene and triethylamine (89.3 and 88.3%), treatment with p-tosyl azide and triethylamine, and then c) reaction with aqueous sodium hydroxide (85.1 and 79.5%). Stereochemical purities of 3 were confirmed as over 99% pure by GLC analysis after necessary conversions.
  • 12
    • 3142723397 scopus 로고    scopus 로고
    • note
    • 4 (31.7%) was improved to 68.7%.
  • 15
    • 3142732180 scopus 로고    scopus 로고
    • note
    • 3 (quant).
  • 16
    • 3142714574 scopus 로고    scopus 로고
    • note
    • Isolated yields for the three-steps preparation procedure shown in the Ref. 9: For 6a, a) ca. 70%, b) 84.8%, c) 76.4%. For 6b, a) 67.5%, b) 95.2%, c) 63.4%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.