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Volumn 44, Issue 35, 2003, Pages 6613-6615

α-Lithiation-rearrangement of N-toluenesulfonyl aziridines with sec-butyllithium and (-)-sparteine: Opposite sense of asymmetric induction to epoxides

Author keywords

Aziridines; Lithiation; Rearrangement; Stereochemistry; Sulfonamides

Indexed keywords

AZIRIDINE DERIVATIVE; EPOXIDE; LITHIUM DERIVATIVE; SPARTEINE;

EID: 0042170072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01677-0     Document Type: Article
Times cited : (26)

References (16)
  • 5
    • 85031136412 scopus 로고    scopus 로고
    • For recent examples, see: (a) Hodgson, D. M.; Stent, M. A. H.; Stefane, B.; Wilson, F. X. Org. Biomol. Chem. 2003, 1, 1139; (b) Hodgson, D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Stent, M. A. H.; Matthews, I. R.; Wilson, F. X.; Witherington, J. Angew. Chem., Int. Ed. 2002, 41, 4313; (c) Hodgson, D. M.; Gras, E. Angew. Chem., Int. Ed. 2002, 41, 2376; (d) Hodgson, D. M.; Cameron, I. D.; Christlieb, M.; Green, R.; Lee, G. P.; Robinson, L. A. J. Chem. Soc., Perkin Trans. 1 2001, 2161; (e) Hodgson, D. M.; Robinson, L. A.; Jones, M. L. Tetrahedron Lett. 1999, 40, 8637; (f) Hodgson, D. M.; Maxwell, C. R.; Matthews, I. R. Tetrahedron: Asymmetry 1999, 10, 1847.
    • For recent examples, see: (a) Hodgson, D. M.; Stent, M. A. H.; Stefane, B.; Wilson, F. X. Org. Biomol. Chem. 2003, 1, 1139; (b) Hodgson, D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Stent, M. A. H.; Matthews, I. R.; Wilson, F. X.; Witherington, J. Angew. Chem., Int. Ed. 2002, 41, 4313; (c) Hodgson, D. M.; Gras, E. Angew. Chem., Int. Ed. 2002, 41, 2376; (d) Hodgson, D. M.; Cameron, I. D.; Christlieb, M.; Green, R.; Lee, G. P.; Robinson, L. A. J. Chem. Soc., Perkin Trans. 1 2001, 2161; (e) Hodgson, D. M.; Robinson, L. A.; Jones, M. L. Tetrahedron Lett. 1999, 40, 8637; (f) Hodgson, D. M.; Maxwell, C. R.; Matthews, I. R. Tetrahedron: Asymmetry 1999, 10, 1847.
  • 16
    • 85031131728 scopus 로고    scopus 로고
    • In Müller's original report (see Ref. 9), the sense of induction in the rearrangement of a norbornene-derived N-tosyl aziridine was established by chemical correlation but the low magnitude of the optical rotation cast potential doubt over this result. However, Müller has now confirmed that this and two new examples are indeed consistent with lithiation of the S-aziridine stereocentre, as we have observed: Müller, P.; Riegert, D.; Bernardinelli, G. personal communication.
    • In Müller's original report (see Ref. 9), the sense of induction in the rearrangement of a norbornene-derived N-tosyl aziridine was established by chemical correlation but the low magnitude of the optical rotation cast potential doubt over this result. However, Müller has now confirmed that this and two new examples are indeed consistent with lithiation of the S-aziridine stereocentre, as we have observed: Müller, P.; Riegert, D.; Bernardinelli, G. personal communication.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.