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Volumn 3, Issue 19, 2001, Pages 2957-2960

Synthesis of medium-sized cyclic amines by selective ring cleavage of sulfonylated bicyclic amines

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; OTONECINE; PYRROLIZIDINE ALKALOID; SULFONE;

EID: 0035922363     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0162163     Document Type: Article
Times cited : (34)

References (29)
  • 1
    • 0035936757 scopus 로고    scopus 로고
    • Most of the recent precedents on synthesis of medium-sized cyclic amines are based on ring closing methathesis procedures; see for instance: (a) Meyers, A. I.; Downing, S. V.; Weiser, M. J. J. Org. Chem. 2001, 66, 1413.
    • (2001) J. Org. Chem. , vol.66 , pp. 1413
    • Meyers, A.I.1    Downing, S.V.2    Weiser, M.J.3
  • 7
    • 0035932581 scopus 로고    scopus 로고
    • ring opening of bicyclic compounds
    • For other recent synthetic approaches, see for instance: (g) Donohoe, T. J.; Raoof, A.; Linney, I. D.; Helliwell, M. Org. Lett. 2001, 3, 861 (ring opening of bicyclic compounds),
    • (2001) Org. Lett. , vol.3 , pp. 861
    • Donohoe, T.J.1    Raoof, A.2    Linney, I.D.3    Helliwell, M.4
  • 19
    • 0033609760 scopus 로고    scopus 로고
    • For reviews on desulfonylation reactions and Julia reactions, see: (a) Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
    • (1999) Tetrahedron , vol.55 , pp. 10547
    • Nájera, C.1    Yus, M.2
  • 25
    • 0343930698 scopus 로고    scopus 로고
    • For the preparation of the starting amino-protected butyraldehyde, see Supporting Information
    • (c) Carretero, J. C.; Gómez Arrayás, R.; Storch de Gracia, I. Tetrahedron Lett. 1996, 37, 3379. For the preparation of the starting amino-protected butyraldehyde, see Supporting Information.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3379
    • Carretero, J.C.1    Gómez Arrayás, R.2    Storch De Gracia, I.3
  • 26
    • 0041793724 scopus 로고    scopus 로고
    • note
    • In all cases similar results were obtained by using methyl iodide or methyl triflate as alkylating agents. A large excess of these reagents (5 or 2 equiv, respectively) was required in order to ensure the complete methylation of the starting amine.
  • 28
    • 0042795848 scopus 로고    scopus 로고
    • note
    • 3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.