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Volumn , Issue 11, 2007, Pages 1702-1706

Enantioselective synthesis of 2-phenyl-9-oxabispidines

Author keywords

9 oxabispidines; Bicyclic compounds; Heterocycles; Sparteine; Stereoselective synthesis

Indexed keywords

9-OXABISPIDINES; BICYCLIC COMPOUNDS; HETEROCYCLES; SPARTEINE; STEREOSELECTIVE SYNTHESIS;

EID: 34250369590     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-966040     Document Type: Article
Times cited : (14)

References (51)
  • 32
    • 33748480130 scopus 로고    scopus 로고
    • For a recent application in natural product synthesis, see
    • (d) For a recent application in natural product synthesis, see: Tambar, U. K.; Ebner, D. C.; Stoltz, B. M. J. Am. Chem. Soc 2006, 128, 11752.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 11752
    • Tambar, U.K.1    Ebner, D.C.2    Stoltz, B.M.3
  • 33
    • 34250310201 scopus 로고    scopus 로고
    • The alkaloid (+)-sparteine [(+)-1] is also a natural product, albeit with a low abundance: Orechoff, A.; Rabinowitch, M.; Kolowanowa, R. Ber. Dtsch. Chem. Ges. 1933, 66, 621.
    • The alkaloid (+)-sparteine [(+)-1] is also a natural product, albeit with a low abundance: Orechoff, A.; Rabinowitch, M.; Kolowanowa, R. Ber. Dtsch. Chem. Ges. 1933, 66, 621.
  • 34
    • 0024697050 scopus 로고    scopus 로고
    • 11,12 and by reduction and resolution of the naturally occurring alkaloid rac-lupanine, see: Ebner, T.; Eichelbaum, M.; Fischer, P.; Meese, C. O. Arch. Pharm. (Weinheim) 1989, 322, 399.
    • 11,12 and by reduction and resolution of the naturally occurring alkaloid rac-lupanine, see: Ebner, T.; Eichelbaum, M.; Fischer, P.; Meese, C. O. Arch. Pharm. (Weinheim) 1989, 322, 399.
  • 43
    • 0344084118 scopus 로고    scopus 로고
    • Several other diamines have been screened in the enantioselective deprotonation of N-Boc-pyrrolidine, but all provided significantly lower levels of enantioselection: (a) Hermet, J. R.; Porter, D. W.; Dearden, M. J.; Harrison, J. R.; Koplin, T.; O'Brien, P.; Parmene, J.; Tyurin, V.; Whitwood, A. C.; Gilday, J.; Smith, N. M. Org. Biomol. Chem. 2003, 1, 3977.
    • Several other diamines have been screened in the enantioselective deprotonation of N-Boc-pyrrolidine, but all provided significantly lower levels of enantioselection: (a) Hermet, J. R.; Porter, D. W.; Dearden, M. J.; Harrison, J. R.; Koplin, T.; O'Brien, P.; Parmene, J.; Tyurin, V.; Whitwood, A. C.; Gilday, J.; Smith, N. M. Org. Biomol. Chem. 2003, 1, 3977.
  • 45
    • 0001292753 scopus 로고    scopus 로고
    • The most popular approach, the Mannich reaction of a piperidin-4-one with formaldehyde and an amine, cannot be applied to the enantioselective preparation of chiral 2-substituted bispidines since any stereochemical information in a chirally modified piperidin-4-one is lost under the harsh reaction conditions: Harrison, J. R.; O'Brien, P.; Porter, D. W.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1999, 3623.
    • The most popular approach, the Mannich reaction of a piperidin-4-one with formaldehyde and an amine, cannot be applied to the enantioselective preparation of chiral 2-substituted bispidines since any stereochemical information in a chirally modified piperidin-4-one is lost under the harsh reaction conditions: Harrison, J. R.; O'Brien, P.; Porter, D. W.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1999, 3623.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.