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Volumn 46, Issue 37, 2007, Pages 7098-7100

Metalated nitriles: Internal 1,2-asymmetric induction

Author keywords

Alkylation; Diastereoselectivity; Internal asymmetric induction; Metalated nitriles; Quaternary asymmetric centers

Indexed keywords

ALKYLATION; CHEMICAL BONDS; LITHIUM COMPOUNDS; STEREOSELECTIVITY;

EID: 34848916346     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701550     Document Type: Article
Times cited : (14)

References (35)
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    • b) K. Fuji, Chem. Rev. 1993, 93, 2037.
    • (1993) Chem. Rev , vol.93 , pp. 2037
    • Fuji, K.1
  • 4
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    • Formation of C-C Bonds by Addition of Enolates to Carbonyl Groups: M. Braun in Methoden der Organischen Chemie (Houben/Weyl) 4th ed. 1952-, E21a, 1995, pp. 1603-1666.
    • "Formation of C-C Bonds by Addition of Enolates to Carbonyl Groups": M. Braun in Methoden der Organischen Chemie (Houben/Weyl) 4th ed. 1952-, Vol. E21a, 1995, pp. 1603-1666.
  • 6
    • 84988072919 scopus 로고    scopus 로고
    • Diastereoselective alkylations of acyclic nitriles typically incorporate heteroatoms for additional complexation: a P. Gmeiner, E. Hummel, C. Haubmann, Liebigs Ann. 1995, 1987;
    • Diastereoselective alkylations of acyclic nitriles typically incorporate heteroatoms for additional complexation: a) P. Gmeiner, E. Hummel, C. Haubmann, Liebigs Ann. 1995, 1987;
  • 11
    • 0141631816 scopus 로고    scopus 로고
    • For leading references on the use of chiral ligands in metalated nitrile alkylations, see: a
    • For leading references on the use of chiral ligands in metalated nitrile alkylations, see: a) Y. Suto, N. Kumagai, S. Matsunaga, M. Kanai, M. Shibasaki, Org. Lett. 2003, 5, 3147;
    • (2003) Org. Lett , vol.5 , pp. 3147
    • Suto, Y.1    Kumagai, N.2    Matsunaga, S.3    Kanai, M.4    Shibasaki, M.5
  • 13
  • 23
    • 34848898414 scopus 로고    scopus 로고
    • Although the alkylations were performed on a racemate, conjugate reduction yields chiral, β-substituted nitriles in high enantiomeric purity: D. Lee, D. Kim, J. Yun, Angew. Chem. 2006, 118, 2851;
    • Although the alkylations were performed on a racemate, conjugate reduction yields chiral, β-substituted nitriles in high enantiomeric purity: D. Lee, D. Kim, J. Yun, Angew. Chem. 2006, 118, 2851;
  • 24
    • 33746216296 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 2785.
    • (2006) Chem. Int. Ed , vol.45 , pp. 2785
    • Angew1
  • 27
    • 34848906217 scopus 로고    scopus 로고
    • 1H NMR spectroscopic analysis of the crude reaction mixture failed to identify any diastereomer;
    • 1H NMR spectroscopic analysis of the crude reaction mixture failed to identify any diastereomer;
  • 28
    • 34848847790 scopus 로고    scopus 로고
    • stereochemical assignment is based on X-ray crystallography of a derivative see the Supporting Information
    • b) stereochemical assignment is based on X-ray crystallography of a derivative (see the Supporting Information).
  • 32
    • 34848873721 scopus 로고    scopus 로고
    • The configurations of 3b and 3c were secured by chemical correlation with that of the ester nitrile 3a as outlined in the Supporting Information.
    • The configurations of 3b and 3c were secured by chemical correlation with that of the ester nitrile 3a as outlined in the Supporting Information.
  • 33
    • 0006381342 scopus 로고    scopus 로고
    • Employed as a racemate, although potentially available in either enantiomeric series: M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25.
    • Employed as a racemate, although potentially available in either enantiomeric series: M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25.
  • 35
    • 34848916652 scopus 로고    scopus 로고
    • The configuration of 14 was chemically correlated with that of 3c (Scheme 2).
    • The configuration of 14 was chemically correlated with that of 3c (Scheme 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.