메뉴 건너뛰기




Volumn 65, Issue 10, 2000, Pages 2856-2862

Additions of enantiopure α-sulfinyl carbanions to (S)-N-sulfinimines: Asymmetric synthesis of β-amino sulfoxides and β-amino alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; SULFOXIDE;

EID: 0000948886     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9903858     Document Type: Article
Times cited : (44)

References (44)
  • 4
    • 0002351924 scopus 로고
    • Doyle, M. P., Ed.; JAI Press: Greenwich, CT
    • (a) Pfaltz, A. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, CT, 1995; pp 61-94.
    • (1995) Advances in Catalytic Processes , pp. 61-94
    • Pfaltz, A.1
  • 12
    • 0000716787 scopus 로고
    • Schreiber, S. L., Ed.; Pergamon Press: Oxford, Chapter 1.12
    • (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 1.12, p 355.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 355
    • Volkmann, R.A.1
  • 13
    • 0001271879 scopus 로고
    • (Houben-Weyl); Helmechen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, E21b, D.1.4
    • (b) Risch, N.; Arend, M. In Stereoselective Synthesis (Houben-Weyl); Helmechen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; E21b, D.1.4, p 1833.
    • (1995) Stereoselective Synthesis , pp. 1833
    • Risch, N.1    Arend, M.2
  • 33
    • 0000027063 scopus 로고
    • Reactions of racemic benzyl tert-butyl sulfoxide with several N-phenylimines are highly stereoselective (see ref 6e). A similar behavior was observed in the synthesis of aziridines from racemic α-halosulfoxides and imines (Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 4093). Racemic fluoromethyl phenyl sulfoxide reacts with N-phenyl arylimines with moderate to very high selectivity, depending on the nature of the aryl group (Mahidol, C.; Reutrakul, V.; Prapansiri, V.; Panyanchotipun, C. Chem. Lett. 1984, 969).
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4093
    • Satoh, T.1    Oohara, T.2    Yamakawa, K.3
  • 34
    • 0002763805 scopus 로고
    • Reactions of racemic benzyl tert-butyl sulfoxide with several N-phenylimines are highly stereoselective (see ref 6e). A similar behavior was observed in the synthesis of aziridines from racemic α-halosulfoxides and imines (Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 4093). Racemic fluoromethyl phenyl sulfoxide reacts with N-phenyl arylimines with moderate to very high selectivity, depending on the nature of the aryl group (Mahidol, C.; Reutrakul, V.; Prapansiri, V.; Panyanchotipun, C. Chem. Lett. 1984, 969).
    • (1984) Chem. Lett. , pp. 969
    • Mahidol, C.1    Reutrakul, V.2    Prapansiri, V.3    Panyanchotipun, C.4
  • 36
    • 0343896747 scopus 로고    scopus 로고
    • 3. Nevertheless, we must take into account that these reactions must be strongly exothermic. Thus, according to the Hammond postulate, one must expect a reactant-like transition state, involving a greater distance for the incipient new C-C bond and thus resulting in a weaker repulsive interaction (Ph/Tol) because of the long distance between the two groups
    • 3. Nevertheless, we must take into account that these reactions must be strongly exothermic. Thus, according to the Hammond postulate, one must expect a reactant-like transition state, involving a greater distance for the incipient new C-C bond and thus resulting in a weaker repulsive interaction (Ph/Tol) because of the long distance between the two groups.
  • 37
    • 0342591087 scopus 로고    scopus 로고
    • 5 and which evidenced a strong decrease in the stereoselectivity of reactions of achiral imines with alkyl p-tolyl sulfoxides
    • 5 and which evidenced a strong decrease in the stereoselectivity of reactions of achiral imines with alkyl p-tolyl sulfoxides.
  • 44
    • 0343896742 scopus 로고    scopus 로고
    • A detailed discusion of the conformational behavior of these substrates appears in ref 25
    • ) A detailed discusion of the conformational behavior of these substrates appears in ref 25.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.