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Volumn 53, Issue 51, 1997, Pages 17527-17542

Stereocontrolled synthesis of functionalised cyclohexanes via the lithium amide-mediated rearrangement of a meso 4,5-disubstituted cyclohexene oxide

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE;

EID: 0030735424     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10201-0     Document Type: Article
Times cited : (16)

References (25)
  • 4
    • 85036678927 scopus 로고    scopus 로고
    • unpublished results
    • Recent results from our laboratory indicate that epoxide 1 prepared by Krow (via m-CPBA epoxidation of the corresponding cyclohexene) was almost certainly a 90:10 mixture of trans-and cis-1; de Sousa, S. E.; Poumellec, P.; O'Brien, P. unpublished results.
    • De Sousa, S.E.1    Poumellec, P.2    O'Brien, P.3
  • 11
    • 85036679671 scopus 로고    scopus 로고
    • note
    • Cis-4,5-di(hydroxymethyl)cyclohexene can be bought from from Lancaster Synthesis Ltd.
  • 12
    • 0343160769 scopus 로고    scopus 로고
    • McClure, C. K.; Chenault, H. K. J. Chem. Educ., 1996, 73, 467-470; Von Langen, D. J.; Tolman, R. L. Tetrahedron: Asymm., 1997, 8, 677-681. For reduction of the corresponding diacid, see: Nagao, Y.; Ikeda, T.; Inoue, T.; Yagi, M.; Shiro, M.; Fujita, E. J. Org. Chem., 1985, 50, 4072-4080.
    • (1996) J. Chem. Educ. , vol.73 , pp. 467-470
    • McClure, C.K.1    Chenault, H.K.2
  • 13
    • 0031053678 scopus 로고    scopus 로고
    • McClure, C. K.; Chenault, H. K. J. Chem. Educ., 1996, 73, 467-470; Von Langen, D. J.; Tolman, R. L. Tetrahedron: Asymm., 1997, 8, 677-681. For reduction of the corresponding diacid, see: Nagao, Y.; Ikeda, T.; Inoue, T.; Yagi, M.; Shiro, M.; Fujita, E. J. Org. Chem., 1985, 50, 4072-4080.
    • (1997) Tetrahedron: Asymm. , vol.8 , pp. 677-681
    • Von Langen, D.J.1    Tolman, R.L.2
  • 14
    • 0001481397 scopus 로고
    • McClure, C. K.; Chenault, H. K. J. Chem. Educ., 1996, 73, 467-470; Von Langen, D. J.; Tolman, R. L. Tetrahedron: Asymm., 1997, 8, 677-681. For reduction of the corresponding diacid, see: Nagao, Y.; Ikeda, T.; Inoue, T.; Yagi, M.; Shiro, M.; Fujita, E. J. Org. Chem., 1985, 50, 4072-4080.
    • (1985) J. Org. Chem. , vol.50 , pp. 4072-4080
    • Nagao, Y.1    Ikeda, T.2    Inoue, T.3    Yagi, M.4    Shiro, M.5    Fujita, E.6
  • 17
    • 0030605867 scopus 로고    scopus 로고
    • O'Brien, P.; Poumellec, P. Tetrahedron Lett., 1996, 37, 5619-5622; de Sousa, S. E.; O'Brien, P.; Poumellec, P. Tetrahedron: Asymm., 1997, 38, 2613-2618.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5619-5622
    • O'Brien, P.1    Poumellec, P.2
  • 19
    • 0030864050 scopus 로고    scopus 로고
    • Asami, M.; Suga, T.; Honda, K.; Inoue, S Tetrahedron Lett., 1997, 38, 6425-6428; Asami, M.; Ishizaki, T.; Inoue, S Tetrahedron Asymm., 1994, 5, 793-796; Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6425-6428
    • Asami, M.1    Suga, T.2    Honda, K.3    Inoue, S.4
  • 20
    • 0028337769 scopus 로고
    • Asami, M.; Suga, T.; Honda, K.; Inoue, S Tetrahedron Lett., 1997, 38, 6425-6428; Asami, M.; Ishizaki, T.; Inoue, S Tetrahedron Asymm., 1994, 5, 793-796; Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408.
    • (1994) Tetrahedron Asymm. , vol.5 , pp. 793-796
    • Asami, M.1    Ishizaki, T.2    Inoue, S.3
  • 21
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    • Asami, M.; Suga, T.; Honda, K.; Inoue, S Tetrahedron Lett., 1997, 38, 6425-6428; Asami, M.; Ishizaki, T.; Inoue, S Tetrahedron Asymm., 1994, 5, 793-796; Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408.
    • (1990) Bull. Chem. Soc. Jpn. , vol.63 , pp. 1402-1408
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  • 25
    • 0025131956 scopus 로고
    • Leonard has also used a similar difference in reactivity between diastereomeric exo and endo spiro epoxides derived from cis-bicyclo[3.3.0]octan-3,7-dione to effect their separation: Leonard, J.; Hewitt, J. D.; Ouali, D.; Simpson, S. J.; Newton, R. F. Tetrahedron Lett., 1990, 31, 6703-6706.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6703-6706
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.