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Volumn , Issue 15, 2004, Pages 2560-2566

α-methylene-β-trichloroacetylamino alkanoates from trichloroacetimidates of the Baylis-Hillman adducts

Author keywords

Amides; Amino acids; Cyclization; Rearrangement; Stereoselectivity

Indexed keywords

CATALYSIS; COMPUTATIONAL METHODS; ESTERS; THERMAL EFFECTS;

EID: 7644237618     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831235     Document Type: Article
Times cited : (26)

References (55)
  • 6
    • 7644237919 scopus 로고    scopus 로고
    • German Patent 2155113, 1972
    • (b) Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174.
    • Baylis, A.B.1    Hillman, M.E.D.2
  • 7
    • 4243830773 scopus 로고
    • (b) Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174.
    • (1972) Chem. Abstr. , vol.77 , pp. 34174
  • 39
    • 7644221580 scopus 로고    scopus 로고
    • note
    • 3, 50 MHz): δ = 19.5, 24.0, 26.8, 28.9, 32.0, 37.8, 48.7, 54.4, 77.2, 166.1.
  • 40
    • 7644236710 scopus 로고    scopus 로고
    • note
    • a values and the geometry of both reactants and products were fully optimized at B3LYP/6-31G* theory level: 1c, ΔE 14.08 kcal/mol; 1d, ΔE 13.51 kcal/mol; 1b, ΔE 5.09 kcal/mol; 1e, ΔE 4.59 kcal/mol; 1a, ΔE 0.0 kcal/mol; 1g, ΔE -3.98 kcal/mol; 1i, ΔE -5.46 kcal/mol; 1h, ΔE -5.76 kcal/mol; 1k, ΔE -5.51 kcal/mol; 1j, ΔE -5.71 kcal/mol. For leading references, see:
  • 49
    • 7644237649 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of the ethyl derivatives 5b,d,f,k, where a multiplet or a double quartet collapsing at 50 °C into a quartet takes place for the ethyl quartet.
  • 51
    • 1642538412 scopus 로고    scopus 로고
    • A concerted four-centers mechanism cannot be excluded, and investigation is currently underway. For a similar reaction recently reported in the literature, see: Mamaghani, M.; Badrian, A. Tetrahedron Lett. 2004, 45, 1547.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1547
    • Mamaghani, M.1    Badrian, A.2
  • 53
    • 0010423366 scopus 로고
    • Amination reactions promoted by electrophiles
    • Helmchen, G.; Hofmann, R. W.; Mulzer, J.; Schauman, E., Eds.; Thieme: Stuttgart
    • (b) Orena, M. Amination Reactions Promoted by Electrophiles, In Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis, Vol. E 21e; Helmchen, G.; Hofmann, R. W.; Mulzer, J.; Schauman, E., Eds.; Thieme: Stuttgart, 1995, 5291-5355.
    • (1995) Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis Vol. E 21e , pp. 5291-5355
    • Orena, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.