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Volumn 1, Issue 6, 1999, Pages 837-839

Enantioselective construction of quaternary α-carbon centers on α-amino phosphonates via catalytic asymmetric allylation

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EID: 0001687230     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990679f     Document Type: Article
Times cited : (77)

References (49)
  • 18
    • 23544442924 scopus 로고    scopus 로고
    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart
    • (b) Mikolajczyk, M.; Drawbowicz, J.; Kielbasinski, P. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol 9, p 5701.
    • (1996) Stereoselective Synthesis , vol.9 , pp. 5701
    • Mikolajczyk, M.1    Drawbowicz, J.2    Kielbasinski, P.3
  • 21
    • 4243214426 scopus 로고
    • Tokyo, Japan; The Chemical Society of Japan: Tokyo, Japan
    • For examples of catalytic enantioselective construction of a quaternary carbon center at α-position of phosphonates, see: (a) Sawamura, M.; Hamashima, H.; Ito, Y. 65th National Meeting of the Chemical Society of Japan; Tokyo, Japan; The Chemical Society of Japan: Tokyo, Japan, 1993; p 4E402.
    • (1993) 65th National Meeting of the Chemical Society of Japan
    • Sawamura, M.1    Hamashima, H.2    Ito, Y.3
  • 23
    • 0002795445 scopus 로고
    • Ojima, I., Ed.; VCH Publishers: New York
    • For reviews, see: (a) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York. 1994; p 325.
    • (1994) Catalytic Asymmetric Synthesis , pp. 325
    • Hayashi, T.1
  • 26
    • 0010441430 scopus 로고    scopus 로고
    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart
    • (d) Lübbers, T.; Metz, P. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 4, p 2371.
    • (1996) Stereoselective Synthesis , vol.4 , pp. 2371
    • Lübbers, T.1    Metz, P.2
  • 41
    • 85034151801 scopus 로고    scopus 로고
    • note
    • 4, and evaporated under reduced pressure. The residue was purified by preparative TLC (EtOAc/MeOH = 10/1), giving 3.
  • 42
    • 85034119175 scopus 로고    scopus 로고
    • note
    • The palladium catalyst prepared in situ from [Pd(π-allyl)Cl]2 was also effective for the asymmetric reaction to give 86% ee of 3a. However, the reaction rate was somewhat slow.
  • 43
    • 85034152612 scopus 로고    scopus 로고
    • note
    • The allylation of 1a with 1.5 equiv of 2a proceeded much slower (78% yield for 48 h), and the enantiomeric excess of the product was 84%.
  • 45
    • 85034147643 scopus 로고    scopus 로고
    • note
    • 4 (EtOAc), and the eluent was evaporated under reduced pressure. The residue was purified by medium-pressure liquid chromatography after passing through a short column of silica gel, giving 6.
  • 48
    • 85034127377 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the O-methylmandelate derivative of syn-6 according to Trost's procedure (see ref 20). Further details are described in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.