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Volumn 75, Issue 18, 2010, Pages 6173-6181

Lewis acid catalyzed highly stereoselective domino-ring-opening cyclization of activated aziridines with enolates: Synthesis of functionalized chiral γ-lactams

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINES; DIASTEREOSELECTIVE; ENANTIO; ENOLATES; FUNCTIONALIZED; GOOD YIELD; LEWIS ACID; METHYLENE CARBONS; RING OPENING; STEREO-SELECTIVE;

EID: 77956540845     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101004x     Document Type: Article
Times cited : (78)

References (83)
  • 36
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    • For synthesis of γ-lactam from enantiopure N, O -ditosylates of amino acids via intermediacy of aziridine, see
    • For synthesis of γ-lactam from enantiopure N, O -ditosylates of amino acids via intermediacy of aziridine, see: Tseng, C. C.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1977, 25, 29
    • (1977) Chem. Pharm. Bull. , vol.25 , pp. 29
    • Tseng, C.C.1    Terashima, S.2    Yamada, S.3
  • 38
    • 77956513380 scopus 로고    scopus 로고
    • note
    • An inseparable mixture of diastereomers was obtained in the above cases.
  • 39
    • 0345975526 scopus 로고    scopus 로고
    • For racemic synthesis of γ-lactam from aziridine, see:, and references cited therein
    • For racemic synthesis of γ-lactam from aziridine, see: Stamm, H. J. Prakt. Chem. 1999, 341, 319 and references cited therein
    • (1999) J. Prakt. Chem. , vol.341 , pp. 319
    • Stamm, H.1
  • 47
    • 79953274306 scopus 로고    scopus 로고
    • Yudin A.K., Ed.; Wiley-VCH: Weinheim,; Chapter 7, p. For some recent reviews on aziridines, see
    • Nielsen, L. P. C.; Jacobsen, E. N. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006; Chapter 7, p 229. For some recent reviews on aziridines, see
    • (2006) Aziridines and Epoxides in Organic Synthesis , pp. 229
    • Nielsen, L.P.C.1    Jacobsen, E.N.2
  • 48
    • 1542375289 scopus 로고    scopus 로고
    • references cited therein
    • Hu, X. E. Tetrahedron 2004, 60, 2701 and references cited therein
    • (2004) Tetrahedron , vol.60 , pp. 2701
    • Hu, X.E.1
  • 79
    • 77956496318 scopus 로고    scopus 로고
    • note
    • For the mechanism of ring-opening cyclization of alkylaziridine, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.