메뉴 건너뛰기




Volumn 68, Issue 19, 2003, Pages 7535-7537

Palladium-catalyzed aerobic oxidative kinetic resolution of alcohols with an achiral exogenous base

Author keywords

[No Author keywords available]

Indexed keywords

OXIDATION; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS;

EID: 0141789726     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034717r     Document Type: Article
Times cited : (78)

References (29)
  • 14
    • 0141847443 scopus 로고    scopus 로고
    • note
    • At low (-)-sparteine concentrations where deprotonation is both rate determining and enantiodetermining, exogenous (-)-sparteine acts as a chiral Brønsted base. See ref 5b for details.
  • 17
    • 0141624122 scopus 로고    scopus 로고
    • note
    • Acetate was introduced into the reaction as the counterion on Pd and the resulting kinetic resolution proved to be poor. See ref 5b for details.
  • 18
    • 85050296727 scopus 로고
    • Kinetic resolution
    • rel = ln[(1 - C)(1 - ee)]/ln[(1 - C)(1 + ee)], where C = conversion and ee = enantiomeric excess. See: Kagan, H. B.; Fiaud, J. C. Kinetic Resolution. Top. Stereochem. 1988, 18, 249.
    • (1988) Top. Stereochem. , vol.18 , pp. 249
    • Kagan, H.B.1    Fiaud, J.C.2
  • 19
    • 0141735939 scopus 로고    scopus 로고
    • note
    • 3, 0.25 mmol (1.0 equiv) of the alcohol or meso diol, and 25 mg of freshly activated crushed molecular sieves (3 Å) were combined. The flask was then attached to the bottom of a reflux condenser. A balloon filled with oxygen gas was then attached to the top of the condenser via a three-way joint. The apparatus was then evacuated (water aspirator) and refilled with oxygen from the balloon three times and heated in an oil bath at 65 °C. Aliquots (0.1 mL) of the reaction were then periodically taken via syringe. The aliquot was quenched with 2% TFA/methanol. The sample was analyzed with use of a GC or HPLC equipped with a chiral column.
  • 20
    • 0037420342 scopus 로고    scopus 로고
    • For examples of nonenzymatic desymmetrization of meso diols, see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2410
    • Trost, B.M.1    Mino, T.2
  • 29
    • 0141735937 scopus 로고    scopus 로고
    • note
    • See Supporting Information for the isolation, characterization, and X-ray structural data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.