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Volumn 17, Issue 12, 2006, Pages 1793-1811

Homochiral lithium amides for the asymmetric synthesis of β-amino acids

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLBENZYLAMINE; AMIDE; BETA AMINO ACID; BUTYRIC ACID; ESTER; LEUCINE; LITHIUM; OCTANOIC ACID; PHENYLALANINE; VALERIC ACID;

EID: 33746456336     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.05.008     Document Type: Article
Times cited : (83)

References (92)
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    • For selected other papers see:
    • For selected other papers see:. Dado G.P., and Gellman S.H. J. Am. Chem. Soc. 116 (1994) 1054
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1054
    • Dado, G.P.1    Gellman, S.H.2
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    • 0037201534 scopus 로고    scopus 로고
    • For a recent review see:
    • For a recent review see:. Liu M., and Sibi M.P. Tetrahedron 58 (2002) 7991
    • (2002) Tetrahedron , vol.58 , pp. 7991
    • Liu, M.1    Sibi, M.P.2
  • 40
    • 0037433606 scopus 로고    scopus 로고
    • For recent advances using chiral ligand controlled asymmetric conjugate addition of lithium amides see:
    • For recent advances using chiral ligand controlled asymmetric conjugate addition of lithium amides see:. Doi H., Sakai T., Iguchi M., Yamada K.-I., and Tomioka K. J. Am. Chem. Soc. 125 (2003) 2886
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2886
    • Doi, H.1    Sakai, T.2    Iguchi, M.3    Yamada, K.-I.4    Tomioka, K.5
  • 63
    • 0032514513 scopus 로고    scopus 로고
    • This allows for selective N-benzyl group deprotection; see:
    • This allows for selective N-benzyl group deprotection; see:. Davies S.G., and Ichihara O. Tetrahedron Lett. 39 (1998) 6045
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6045
    • Davies, S.G.1    Ichihara, O.2
  • 82
    • 33746456713 scopus 로고    scopus 로고
    • note
    • Wittig Olefination gave a 95:5 mixture of (E:Z) isomers, with purification to homogeneity giving the desired (E)-isomer in 76% isolated yield and with a >99:1 (E:Z) ratio.
  • 83
    • 33746467783 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the crude reaction product did not allow calculation of the diastereoselectivity of this reaction; but given the extensive precedent for the high stereoselectivity of this conjugate addition reaction, and the ee of the derived product 64, a diastereoselectivity of >95% was assumed.
  • 84
    • 33746434757 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy and in comparison with racemic material.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.