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Volumn 46, Issue 13, 2005, Pages 2239-2242

Kinetic resolution of sec-alcohols by a new class of pyridine catalysts having a conformation switch system

Author keywords

Asymmetric acylation; Cation interaction; Conformation switch system; Kinetic resolution; Organocatalyst

Indexed keywords

ALCOHOL; PYRIDINE;

EID: 14744296806     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.019     Document Type: Article
Times cited : (90)

References (42)
  • 32
    • 0033601313 scopus 로고    scopus 로고
    • Preparation of (S)-4-tert-butyl-1,3-thiazolidine-2-thione, see: S. Yamada, and H. Katsumata J. Org. Chem. 64 1999 9365
    • (1999) J. Org. Chem. , vol.64 , pp. 9365
    • Yamada, S.1    Katsumata, H.2
  • 37
    • 85030809465 scopus 로고    scopus 로고
    • note
    • Triethylamine was used instead of collidine because of little difference in the selectivities
  • 38
    • 85030817740 scopus 로고    scopus 로고
    • note
    • The N-isobutyryl form of 1a is in equilibrium with 1a, in addition, the chemical shifts of the pyridinium protons receive an anisotropic effect from the N-acyl carbonyl group. Therefore, N-methylpyridinium salt 5 was used instead of N-isobutyryl form of 1a to neglect such inadequate effects for evaluation of the intramolecular interaction
  • 39
    • 85030814168 scopus 로고    scopus 로고
    • note
    • NOE experiments of N-isobutyryl form of 1a clarified that the N-acyl carbonyl oxygen is close to H6. Irradiation of H2 and H6 resulted in 17.6% and 0.5% NOEs for COCH proton, respectively
  • 40
    • 85030810193 scopus 로고    scopus 로고
    • note
    • DFT calculations at the B3LYP/6-31G* level suggested that conformer A where the CS group blocks the A-side of the pyridinium is 1.02 kcal/mol more stable than conformer B


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.