메뉴 건너뛰기




Volumn 43, Issue 30, 2004, Pages 3952-3954

General catalytic synthesis of highly enantiomerically enriched terminal aziridines from racemic epoxides

Author keywords

Asymmetric catalysis; Aziridines; Nitrogen heterocycles; Small ring systems; Sulfonamides

Indexed keywords

ALCOHOLS; AMINO ACIDS; CATALYSIS; COBALT COMPOUNDS; DERIVATIVES; SYNTHESIS (CHEMICAL);

EID: 4544268904     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460369     Document Type: Article
Times cited : (85)

References (40)
  • 1
    • 0036374173 scopus 로고    scopus 로고
    • For reviews on the preparation and reactions of aziridines, see: a) J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247-258;
    • (2002) Chem. Soc. Rev. , vol.31 , pp. 247-258
    • Sweeney, J.B.1
  • 5
    • 0000400367 scopus 로고
    • e) D. Tanner, Angew. Chem. 1994, 106, 625-646; Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619;
    • (1994) Angew. Chem. , vol.106 , pp. 625-646
    • Tanner, D.1
  • 6
    • 33748605775 scopus 로고
    • e) D. Tanner, Angew. Chem. 1994, 106, 625-646; Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 599-619
  • 8
    • 0000673216 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • g) E. N. Jacobsen in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 607-618;
    • (1999) Comprehensive Asymmetric Catalysis, Vol. 2 , vol.2 , pp. 607-618
    • Jacobsen, E.N.1
  • 11
    • 0030590954 scopus 로고    scopus 로고
    • Moderate-to-high ee values have been reported only in the direct aziridination of styrene: a) H. Nishikori, T. Katsuki, Tetrahedron Lett. 1996, 37, 9245-9248;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9245-9248
    • Nishikori, H.1    Katsuki, T.2
  • 14
    • 0034697199 scopus 로고    scopus 로고
    • For a review of the synthesis of 1,2-amino alcohols, see: S. C. Bergmeier, Tetrahedron 2000, 56, 2561-2576.
    • (2000) Tetrahedron , vol.56 , pp. 2561-2576
    • Bergmeier, S.C.1
  • 21
    • 4544234934 scopus 로고    scopus 로고
    • note
    • Simultaneous addition of the two reagents led to inferior results, consistent with the observation that the rates of epoxide hydrolysis and ring-opening with 2 are competitive.
  • 22
    • 4544360262 scopus 로고    scopus 로고
    • note
    • Synthesis of 7b under Mitsunobu conditions proceeded in low yield (44%) as a result of the instability of the nosylaziridine to the reaction conditions.
  • 29
    • 4544247901 scopus 로고    scopus 로고
    • note
    • Compound 7e undergoes decomposition upon storage as a neat liquid, but was stored safely for prolonged periods as a frozen 0.78 M solution in benzene at -30°C.
  • 30
    • 3242885481 scopus 로고    scopus 로고
    • a) A. Ricci, M. Fochi, Angew. Chem. 2003, 115, 1482-1484; Angew. Chem. Int. Ed. 2003, 42, 1444-1446;
    • (2003) Angew. Chem. , vol.115 , pp. 1482-1484
    • Ricci, A.1    Fochi, M.2
  • 31
    • 0037418988 scopus 로고    scopus 로고
    • a) A. Ricci, M. Fochi, Angew. Chem. 2003, 115, 1482-1484; Angew. Chem. Int. Ed. 2003, 42, 1444-1446;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1444-1446
  • 32
    • 4544279065 scopus 로고
    • b) G. Köbrich, P. Buck, Angew. Chem. 1966, 78, 1062-1063; Angew. Chem. Int. Ed. Engl. 1966, 5, 1044.
    • (1966) Angew. Chem. , vol.78 , pp. 1062-1063
    • Köbrich, G.1    Buck, P.2
  • 33
    • 84981826716 scopus 로고
    • b) G. Köbrich, P. Buck, Angew. Chem. 1966, 78, 1062-1063; Angew. Chem. Int. Ed. Engl. 1966, 5, 1044.
    • (1966) Angew. Chem. Int. Ed. Engl. , vol.5 , pp. 1044
  • 38
    • 4544226397 scopus 로고    scopus 로고
    • note
    • 3 reaction required 23 h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.