메뉴 건너뛰기




Volumn 121, Issue 38, 1999, Pages 8959-8960

Asymmetric synthesis of β-amino acid derivatives via catalytic conjugate addition of hydrazoic acid to unsaturated imides [10]

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; BETA AMINO ACID; HYDRAZIDE DERIVATIVE; IMIDE; METAL COMPLEX;

EID: 0033615304     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991621z     Document Type: Letter
Times cited : (299)

References (30)
  • 5
    • 0030785114 scopus 로고    scopus 로고
    • For reviews, see: (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
    • (1997) Chem. Commun. , pp. 2015
    • Seebach, D.1    Matthews, J.L.2
  • 6
    • 0542421525 scopus 로고    scopus 로고
    • For reviews, see: (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 173
    • Gellman, S.H.1
  • 13
    • 0032554058 scopus 로고    scopus 로고
    • For recent advances, see: (a) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. I 1996, 2823. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 431
    • Kobayashi, S.1    Ishitani, H.2    Ueno, M.3
  • 15
    • 0033593425 scopus 로고    scopus 로고
    • (d) While this manuscript was in preparation, the Detty group reported moderate (up to 46%) enantioselectivity in the conjugate addition of amines with chiral (salen)Cu(II) complexes: Zhou, F.; Detty, M. R.; Lachicotte, R. J. Tetrahedron Lett. 1999, 40, 585.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 585
    • Zhou, F.1    Detty, M.R.2    Lachicotte, R.J.3
  • 23
    • 0000761191 scopus 로고
    • The preparation and handling of hydrazoic acid solutions are described H. Wolff (Org. React. 1946, 3, 307).
    • (1946) Org. React. , vol.3 , pp. 307
    • Wolff, H.1
  • 24
    • 0345519493 scopus 로고    scopus 로고
    • note
    • Of the complexes screened under these conditions (5 mol % catalyst, rt, 48 h), only the corresponding (salen)Al(III) chloride (31% conversion, 28% ee), (salen)Cr(III) azide (23% conversion, 9% ee), and (salen)Ru(III) chloride (46% conversion, 4% ee) proved catalytically active.
  • 27
    • 0344225777 scopus 로고    scopus 로고
    • note
    • The similarly high enantioselectivities obtained with maleimide 4 and acyclic substrates 8a-g suggest a reactive s-trans conformation of the unsaturated imide in the conjugate addition reaction. If a Lewis acid mode of activation involving one-point binding is assumed, a simplified stereochemical model can be devised, such as the one below, that accounts for the observed facial selectivity. (equation presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.