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Volumn 53, Issue 34, 2012, Pages 4518-4521

Naphthyl-substituted bisoxazoline and pyridylbisoxazoline-copper(I) catalysts for asymmetric allylic oxidation

Author keywords

Allylic oxidation; Bisoxazoline copper(I) complex; Naphthyl

Indexed keywords

COPPER; CYCLOHEXENE DERIVATIVE; NAPHTHYL GROUP; OXAZOLINE DERIVATIVE; PYRIDINE;

EID: 84864058347     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.06.010     Document Type: Article
Times cited : (28)

References (46)
  • 41
    • 0007100920 scopus 로고
    • For the preparation of tert-butylhypochlorite, see M.J. Mintz, and C. Walling Org. Synth. Collective Vol. V 1983 183
    • (1983) Org. Synth. , vol.5 , pp. 183
    • Mintz, M.J.1    Walling, C.2
  • 45
    • 0009813872 scopus 로고
    • Allylic oxidation reactions with cyclic alkenes were performed by forming the copper(I) hexafluorophosphate-bisoxazoline complex (Kubas, G. J.; Monzyk, B.; Crumbliss, A. L. Inorg. Synth. 1990, 28, 68) (15 mol %) in degassed acetonitrile (0.2 M) at room temperature and adding 5 equiv of olefin followed by perester (1 equiv) at -20 °C (Tables 1 and 2). The reactions were monitored by TLC for consumption of perester and stopped at the given time. The yields are for isolated materials based on the perester, and the selectivities were determined by chiral HPLC with comparison to racemic material. The ligands were recovered, 85% yield based on the amount used and recycled with comparable results. In all cases the S,S-ligands generated (S)-ester product. Levorotatory allyl alcohols were produced upon hydrolysis (KOH) of the S-enriched benzoate esters. (a) Wahhab, A.; Tavares, D. F.; Rauk, A. Can. J. Chem. 1990, 68, 1559.
    • (1990) Can. J. Chem. , vol.68 , pp. 1559
    • Wahhab, A.1    Tavares, D.F.2    Rauk, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.