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Volumn 42, Issue 3, 2003, Pages 315-317

Amplification of chirality from extremely low to greater than 99.5 % ee by asymmetric autocatalysis

Author keywords

Alkylations; Asymmetric synthesis; Autocatalysis; Chirality; Zinc

Indexed keywords

ALDEHYDES; ALKYLATION;

EID: 0037455228     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390105     Document Type: Article
Times cited : (211)

References (56)
  • 1
    • 0344326234 scopus 로고    scopus 로고
    • a) A. Eschenmoser, Science 1999, 284, 2118-2124;
    • (1999) Science , vol.284 , pp. 2118-2124
    • Eschenmoser, A.1
  • 3
    • 0033521221 scopus 로고    scopus 로고
    • b) B. L. Feringa, R. A. van Delden, Angew. Chem. 1999, 111, 3624-3645; Angew. Chem. Int. Ed. 1999, 38, 3418-3438;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3418-3438
  • 22
    • 0001435829 scopus 로고    scopus 로고
    • for the nonlinear effect in asymmetric autoinduction, see M. Szlosek, M. Figadère, Angew. Chem. 2000, 112, 1869-1871; Angew. Chem. Int. Ed, 2000, 39, 1799-1801;
    • (2000) Angew. Chem. , vol.112 , pp. 1869-1871
    • Szlosek, M.1    Figadère, M.2
  • 23
    • 0039842613 scopus 로고    scopus 로고
    • for the nonlinear effect in asymmetric autoinduction, see M. Szlosek, M. Figadère, Angew. Chem. 2000, 112, 1869-1871; Angew. Chem. Int. Ed, 2000, 39, 1799-1801;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1799-1801
  • 24
    • 0000655043 scopus 로고    scopus 로고
    • reviews: e) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959;
    • (1998) Angew. Chem. , vol.110 , pp. 3088-3127
    • Girard, C.1    Kagan, H.B.2
  • 25
    • 0032538773 scopus 로고    scopus 로고
    • reviews: e) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2922-2959
  • 28
    • 0034675555 scopus 로고    scopus 로고
    • g) K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676-3701; Angew. Chem. Int. Ed. 2000, 39, 3532-3556;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3532-3556
  • 35
    • 0034680593 scopus 로고    scopus 로고
    • e) H. Buschmann, R. Thede, D. Heller, Angew. Chem. 2000, 112, 4197-4199; Angew. Chem. Int. Ed. 2000, 39, 4033-4036;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4033-4036
  • 44
    • 0033105631 scopus 로고    scopus 로고
    • T. Shibata, S. Yonekubo, K. Soai, Angew. Chem. 1999, 111, 749-751; Angew. Chem. Int. Ed. 1999, 38, 659-661.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 659-661
  • 45
    • 0347519304 scopus 로고    scopus 로고
    • note
    • Racemic 1 was prepared by the lithiation of 2-alkynyl-5-bromopyrimidine followed by treatment with 2-methylpropanal.
  • 46
    • 0346888697 scopus 로고    scopus 로고
    • note
    • -3M solution of (S)-1 with ca. 0.00005% ee.
  • 50
    • 0001564142 scopus 로고    scopus 로고
    • -5% ee is below the detection level of the instruments typically used, for example, HPLC, CD, polarimeter etc. (for recent advances in the measurement of enantiomeric excesses, see: b) M. Tsukamoto, H. B. Kagan, Adv. Synth. Catal. 2002, 344, 453-463). 2) Only after obtaining results that the asymmetric autocatalyst with S configuration affords itself with S configuration and the asymmetric autocatalyst with R configuration affords itself with R configuration one can judge that the autocatalyst works.
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 453-463
    • Tsukamoto, M.1    Kagan, H.B.2
  • 51
    • 0346888695 scopus 로고    scopus 로고
    • note
    • -9% ee has been employed, but we have not yet received reproducible results probably because of the effect of some unexpected and unknown chiral factor.
  • 52
    • 0346888696 scopus 로고    scopus 로고
    • note
    • [10a]
  • 55
    • 0034678915 scopus 로고    scopus 로고
    • b) I. Sato, K. Kadowaki, K. Soai, Angew. Chem. 2000, 112, 1570-1572; Angew. Chem. Int. Ed. 2000, 39, 1510-1512;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1510-1512


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.