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Volumn 9, Issue 4, 2011, Pages 1160-1168

Enantiomerically pure 2-aryl(alkyl)-2-trifluoromethylaziridines: Synthesis and ring opening with selected O- and N-nucleophiles

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; AMINO ALCOHOLS; AZIRIDINES; BASIC CONDITIONS; CYCLISATIONS; PROTECTING GROUP; RING OPENING;

EID: 79551655587     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00690d     Document Type: Article
Times cited : (30)

References (48)
  • 12
    • 74949098517 scopus 로고    scopus 로고
    • For reviews on aziridine ring opening, see:
    • H. Pellissier Tetrahedron 2010 66 1509
    • (2010) Tetrahedron , vol.66 , pp. 1509
    • Pellissier, H.1
  • 17
    • 77649239382 scopus 로고    scopus 로고
    • For the preparation of optically active aziridines bearing a trifluoromethyl group, see:
    • P. Lu Tetrahedron 2010 66 2549
    • (2010) Tetrahedron , vol.66 , pp. 2549
    • Lu, P.1
  • 42
    • 34250891949 scopus 로고    scopus 로고
    • For another strategy for the synthesis of β-amino alcohols and β-diamines containing a quaternary trifluoromethyl group, see:
    • J. J. Caldwell D. Craig Angew. Chem., Int. Ed. 2007 46 2631
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2631
    • Caldwell, J.J.1    Craig, D.2
  • 44
    • 61949290562 scopus 로고    scopus 로고
    • The partial racemization of the aziridinium salt through its interconversion with the carbenium ion was ruled out, since a small amount of enantiomerically pure aziridine (S)-6a (16%, ee = 100%) was also recovered For a similar example of acid hydrolysis of N-tosyl-2-phenylaziridine-2-carboxylate at C-2, see:
    • G. Hughes P. O'Shea J. Goll D. Gauvreau J. Steele Tetrahedron 2009 65 3189
    • (2009) Tetrahedron , vol.65 , pp. 3189
    • Hughes, G.1    O'Shea, P.2    Goll, J.3    Gauvreau, D.4    Steele, J.5
  • 46
    • 67650689320 scopus 로고    scopus 로고
    • ee = 97% for the aminoalcohol (R)-5c refects the enantiopurity of the starting ether (R)-4c, no racemization occurred during the deprotection step
    • J. Nonnenmacher F. Grellepois C. Portella Eur. J. Org. Chem. 2009 22 3726
    • (2009) Eur. J. Org. Chem. , vol.22 , pp. 3726
    • Nonnenmacher, J.1    Grellepois, F.2    Portella, C.3
  • 48
    • 77956924656 scopus 로고    scopus 로고
    • As expected, the ring opening of the Bn-aziridine (S)-6c with hydroxide ion or amine was unsuccessful Heating of aziridines (S)-6a,b with aniline (1.2 equiv) under micro-wave irradiation (150 °C) significantly reduced the reaction time (20-40 min) without altering the yield
    • E. Obijalska G. Mloston A. Linden H. Heimgartner Helv. Chim. Acta 2010 93 1725
    • (2010) Helv. Chim. Acta , vol.93 , pp. 1725
    • Obijalska, E.1    Mloston, G.2    Linden, A.3    Heimgartner, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.