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Volumn 133, Issue 25, 2011, Pages 9730-9733

Chiral Brønsted acid-catalyzed asymmetric trisubstituted aziridine synthesis using α-diazoacyl oxazolidinones

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINES; OXAZOLIDINONES; STEREOSELECTIVE SYNTHESIS;

EID: 79959521750     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja203901h     Document Type: Article
Times cited : (90)

References (35)
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    • For a review of Brønsted acid-catalyzed C-C bond formation with diazo compounds, see
    • For a review of Brønsted acid-catalyzed C-C bond formation with diazo compounds, see: Johnston, J. N.; Muchalski, H.; Troyer, T. L. Angew. Chem., Int. Ed. 2010, 49, 2290
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 2290
    • Johnston, J.N.1    Muchalski, H.2    Troyer, T.L.3
  • 18
    • 79959491022 scopus 로고    scopus 로고
    • Our effort to apply chiral Lewis acid catalysts proved to be in vain, as only modest enantioselectivity could be attained, presumably because of the preferential coordination of oxophilic Lewis acids to the Boc moiety (which is distant from the prochiral imine carbon) rather than the nitrogen atom of the imine.
    • Our effort to apply chiral Lewis acid catalysts proved to be in vain, as only modest enantioselectivity could be attained, presumably because of the preferential coordination of oxophilic Lewis acids to the Boc moiety (which is distant from the prochiral imine carbon) rather than the nitrogen atom of the imine.
  • 28
    • 0030860279 scopus 로고    scopus 로고
    • For leading references on hydrolytic kinetic resolution of epoxides, see
    • For leading references on hydrolytic kinetic resolution of epoxides, see: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936
    • (1997) Science , vol.277 , pp. 936
    • Tokunaga, M.1    Larrow, J.F.2    Kakiuchi, F.3    Jacobsen, E.N.4
  • 30
    • 35048832273 scopus 로고    scopus 로고
    • For chiral Brønsted acid-catalyzed desymmetrization of meso -aziridines, see
    • For chiral Brønsted acid-catalyzed desymmetrization of meso -aziridines, see: Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12084
    • Rowland, E.B.1    Rowland, G.B.2    Rivera-Otero, E.3    Antilla, J.C.4
  • 31
    • 70749161701 scopus 로고    scopus 로고
    • Also see: Angew. Chem., Int. Ed. 2009, 48, 2082 and references therein
    • Larson, S. E.; Baso, J. C.; Li, G.; Antilla, J. C. Org. Lett. 2009, 11, 5186 Also see: Schneider, C. Angew. Chem., Int. Ed. 2009, 48, 2082 and references therein
    • (2009) Org. Lett. , vol.11 , pp. 5186
    • Larson, S.E.1    Baso, J.C.2    Li, G.3    Antilla, J.C.4    Schneider, C.5
  • 32
    • 79959505583 scopus 로고    scopus 로고
    • See the Supporting Information for details.
    • See the Supporting Information for details.
  • 33
    • 79959508690 scopus 로고    scopus 로고
    • Hydrolyzed products were not observed in the results showcased in Tables 2 and 3.
    • Hydrolyzed products were not observed in the results showcased in Tables 2 and 3.
  • 34
    • 79955637815 scopus 로고    scopus 로고
    • During the preparation of this manuscript, Antilla and co-workers reported a catalytic asymmetric two-step aza-Darzens reaction to give trisubstituted aziridines having two identical acetyl groups. See
    • During the preparation of this manuscript, Antilla and co-workers reported a catalytic asymmetric two-step aza-Darzens reaction to give trisubstituted aziridines having two identical acetyl groups. See: Larson, S. E.; Li, G.; Rowland, G. B.; Junge, D.; Huang, R.; Woodcock, H. L.; Antilla, J. C. Org. Lett. 2011, 13, 2188
    • (2011) Org. Lett. , vol.13 , pp. 2188
    • Larson, S.E.1    Li, G.2    Rowland, G.B.3    Junge, D.4    Huang, R.5    Woodcock, H.L.6    Antilla, J.C.7
  • 35
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    • After the submission of this manuscript, Huang and Wulff reported the catalytic asymmetric synthesis of trisubstituted aziridines using identical reactions. See
    • After the submission of this manuscript, Huang and Wulff reported the catalytic asymmetric synthesis of trisubstituted aziridines using identical reactions. See: Huang, L.; Wulff, W. D. J. Am. Chem. Soc. 2011, 133, 8892
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 8892
    • Huang, L.1    Wulff, W.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.