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Volumn 9, Issue 7, 2007, Pages 1319-1322

The first enantioenriched metalated nitrile possessing macroscopic configurationat stability

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EID: 34147107497     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070149g     Document Type: Article
Times cited : (31)

References (24)
  • 7
    • 0001505175 scopus 로고    scopus 로고
    • rac = 9.060: Walborsky, H. M.; Motes, J. M. J. Am. Chem. Soc. 1970, 92, 2445-2450.
    • rac = 9.060: Walborsky, H. M.; Motes, J. M. J. Am. Chem. Soc. 1970, 92, 2445-2450.
  • 8
    • 0000609569 scopus 로고    scopus 로고
    • X-ray crystallography of a related lithiated cyclopropylnitrile shows C-lithiation (e.g. 1, Figure 1): Boche, G.; Harms, K.; Marsch, M. J. Am. Chem. Soc. 1988, 110, 6925-6926.
    • (a) X-ray crystallography of a related lithiated cyclopropylnitrile shows C-lithiation (e.g. 1, Figure 1): Boche, G.; Harms, K.; Marsch, M. J. Am. Chem. Soc. 1988, 110, 6925-6926.
  • 9
    • 34147181659 scopus 로고    scopus 로고
    • Enantiopure acyclic nitriles undergo racemizing H-D exchange (ref 3).
    • (b) Enantiopure acyclic nitriles undergo racemizing H-D exchange (ref 3).
  • 14
    • 34147155771 scopus 로고    scopus 로고
    • 1-3 using Walborsky's protocol; percent ee measured by chiral stationary phase HPLC.
    • 1-3 using Walborsky's protocol; percent ee measured by chiral stationary phase HPLC.
  • 15
    • 1342296307 scopus 로고    scopus 로고
    • Eyring equation: Eyring, H, Chem. Rev. 1935, 17, 65-77.
    • Eyring equation: Eyring, H, Chem. Rev. 1935, 17, 65-77.
  • 18
    • 0000376494 scopus 로고    scopus 로고
    • For studies of the configurational stabilities of unstabilized primary alkyl organolithiums and organomagnesiums see: Witanowski, M, Roberts, J. D J. Am. Chem. Soc. 1966, 88, 737-741
    • For studies of the configurational stabilities of unstabilized primary alkyl organolithiums and organomagnesiums see: Witanowski, M.; Roberts, J. D J. Am. Chem. Soc. 1966, 88, 737-741.
  • 20
    • 12344273033 scopus 로고    scopus 로고
    • Walborsky, H. M.; Barash, L.; Young, A. E.; Impastato, F. J. J. Am. Chem. Soc. 1961, 83, 2517-2525. Correlation performed by the quasiracemate method; the absolute (S)-configuration of (+)-4 is correctly noted in ref 6a.
    • Walborsky, H. M.; Barash, L.; Young, A. E.; Impastato, F. J. J. Am. Chem. Soc. 1961, 83, 2517-2525. Correlation performed by the quasiracemate method; the absolute (S)-configuration of (+)-4 is correctly noted in ref 6a.
  • 22
    • 34147116700 scopus 로고    scopus 로고
    • Standard error; at the 95% confidence limit, the % ee values are 81 ± 3 (-100°C) and 77 ± 4 (-78°C), respectively (time = 0 s).
    • Standard error; at the 95% confidence limit, the % ee values are 81 ± 3 (-100°C) and 77 ± 4 (-78°C), respectively (time = 0 s).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.