메뉴 건너뛰기




Volumn 65, Issue 8, 2000, Pages 2580-2582

Unexpected one-pot epoxy sulfone-enaminone transformation. Synthesis of 5a-carba-β-mannopyranosylamine

Author keywords

[No Author keywords available]

Indexed keywords

ENAMINE; EPOXIDE; PYRAN DERIVATIVE; SUGAR;

EID: 0034697086     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991468r     Document Type: Note
Times cited : (22)

References (23)
  • 1
    • 0004067242 scopus 로고
    • Tetrahedron Organic Chemistry Series 10; Pergamon Press: Oxford, U.K
    • Simpkins, N. S. Sulfones in Organic Synthesis; Tetrahedron Organic Chemistry Series 10; Pergamon Press: Oxford, U.K, 1993; pp 56, 362. For other related references, see the following. (a) Durst, T.; Tin, K. C.; de Reinach-Hirtzbach, F.; Decesare, J. M.; Ryan, M. D. Can. J. Chem. 1979, 57, 258-266.
    • (1993) Sulfones in Organic Synthesis , pp. 56
    • Simpkins, N.S.1
  • 2
    • 0001183468 scopus 로고
    • Simpkins, N. S. Sulfones in Organic Synthesis; Tetrahedron Organic Chemistry Series 10; Pergamon Press: Oxford, U.K, 1993; pp 56, 362. For other related references, see the following. (a) Durst, T.; Tin, K. C.; de Reinach-Hirtzbach, F.; Decesare, J. M.; Ryan, M. D. Can. J. Chem. 1979, 57, 258-266.
    • (1979) Can. J. Chem. , vol.57 , pp. 258-266
    • Durst, T.1    Tin, K.C.2    De Reinach-Hirtzbach, F.3    Decesare, J.M.4    Ryan, M.D.5
  • 6
    • 0000652023 scopus 로고
    • For the ring opening of α,β-epoxy sulfones by azide ion, see the following. (a) Barone, A. D.; Snitman, D. L.; Watt, D. S. J. Org. Chem. 1978, 43, 2066-2068.
    • (1978) J. Org. Chem. , vol.43 , pp. 2066-2068
    • Barone, A.D.1    Snitman, D.L.2    Watt, D.S.3
  • 8
    • 33644915171 scopus 로고
    • We thank one of the reviewers for the comment given on the importance of silyl groups to facilitate the epoxide opening
    • Papini, A.; Ricci, A.; Taddei, M.; Seconi, G.; Dembech, P. J. Chem. Soc., Perkin Trans. 1 1984, 2261-2265. We thank one of the reviewers for the comment given on the importance of silyl groups to facilitate the epoxide opening.
    • (1984) J. Chem. Soc., Perkin Trans. 1 , pp. 2261-2265
    • Papini, A.1    Ricci, A.2    Taddei, M.3    Seconi, G.4    Dembech, P.5
  • 11
    • 84985574417 scopus 로고    scopus 로고
    • Chapleur, Y., Ed.; Wiley-VCH: Weinheim
    • For a general account on the chemistry and biological properties of carbasugars, see the following. Ogawa, S. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1998. For some selected synthetic approach to aminocarbasugars, see the following. (a) Paulsen, H.; Heiker, F. R. Angew. Chem., Int. Ed. Engl. 1980, 19, 904-905.
    • (1998) Carbohydrate Mimics: Concepts and Methods
    • Ogawa, S.1
  • 12
    • 84985574417 scopus 로고    scopus 로고
    • For a general account on the chemistry and biological properties of carbasugars, see the following. Ogawa, S. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1998. For some selected synthetic approach to aminocarbasugars, see the following. (a) Paulsen, H.; Heiker, F. R. Angew. Chem., Int. Ed. Engl. 1980, 19, 904-905.
    • (1980) Angew. Chem., Int. Ed. Engl. , vol.19 , pp. 904-905
    • Paulsen, H.1    Heiker, F.R.2
  • 18
    • 0029149970 scopus 로고
    • For the biological importance and previous synthesis of validamine and some stereoisomers see the references quoted in refs 2, 5, and the following. (a) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332-5334.
    • (1995) J. Org. Chem. , vol.60 , pp. 5332-5334
    • Shing, T.K.M.1    Tai, V.W.-F.2
  • 22
    • 0343175855 scopus 로고
    • Oxford Science Publications: Oxford, U.K., Chapter 4
    • For a discussion of the generation of nitrenes from azides and 1,2 hydrogen shifts in these systems, see the following. Moody, Ch. J.; Whitham, G. H. In Reactive Intermediates; Oxford Science Publications: Oxford, U.K., 1995; Chapter 4, pp 52-53, 61-62.
    • (1995) Reactive Intermediates , pp. 52-53
    • Moody, Ch.J.1    Whitham, G.H.2
  • 23
    • 0342741391 scopus 로고    scopus 로고
    • note
    • We thank one of the reviewers for suggesting the experiment starting from 1b in order to clarify the proposed mechanism.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.