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Volumn 64, Issue 6, 1999, Pages 2003-2009

Radical cyclization in heterocycle synthesis. 6. A new entry to cyclic amino alcohols via stannyl radical cyclization of oxime ethers connected with aldehydes or ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINOALCOHOL; AMINOCYCLITOL; AMINOSUGAR; DAUNOSAMINE; DYSIHERBAINE; ETHER; KETONE; OXIME; PSEUDODISTOMIN A; TREHAZOLAMINE; TRIBUTYLTIN; UNCLASSIFIED DRUG;

EID: 0033583281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9822176     Document Type: Article
Times cited : (49)

References (64)
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    • Translated by Lomas, J.; John Wiley & Sons Inc.: New York
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  • 18
    • 77956697188 scopus 로고    scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • (d) Ninomiya, I.; Kiguchi, T.; Naito, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1998; Vol. 50, pp 317-342.
    • (1998) The Alkaloids , vol.50 , pp. 317-342
    • Ninomiya, I.1    Kiguchi, T.2    Naito, T.3
  • 32
    • 0344887831 scopus 로고    scopus 로고
    • note
    • We have also reported that the geometry of the oxime ether group does not influence the stereoselectivity in its radical cyclization, see ref 1.
  • 34
    • 0000860816 scopus 로고
    • For selected examples of the radical cyclization of O-stannyl ketyl radical to alkenes, see: (a) Enholm, E. J.; Prasad, G. Tetrahedron, Lett. 1989, 30, 4939-4942.
    • (1989) Tetrahedron, Lett. , vol.30 , pp. 4939-4942
    • Enholm, E.J.1    Prasad, G.2
  • 58
    • 0002047232 scopus 로고    scopus 로고
    • For our recent works in intermolecular radical addition to oxime ethers, see: (a) Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789-1790.
    • (1997) Chem. Commun. , pp. 1789-1790
    • Miyabe, H.1    Ushiro, C.2    Naito, T.3
  • 61
    • 0344024864 scopus 로고    scopus 로고
    • note
    • In the electroreductive cyclization of oxime ethers connected by a tether to aldehydes, the trans-selectivity was explained by the electronic repulsion between negative charge located on the oxygen and nitrogen atom in the oxime ethers, see ref 10.
  • 62
    • 0344887824 scopus 로고    scopus 로고
    • note
    • Recently Fu group has reported that cis-selectivity is observed in stannyl radical addition-cyclization of dicarbonyl compounds and is explained via 1,3,2-dioxastannolane as a cyclic intermediate, see ref 14.
  • 63
    • 4243481130 scopus 로고
    • U.S. Patent 3920772, 1975
    • Stach, L. J. U.S. Patent 3920772, 1975 (Chem. Abstr. 1976, 84, 89603d).
    • (1976) Chem. Abstr. , vol.84
    • Stach, L.J.1
  • 64
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    • note
    • See the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.