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Volumn 15, Issue 23, 2004, Pages 3693-3697

Development of a novel chiral spiro ligand bearing oxazoline

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; COPPER DERIVATIVE; LIGAND; N BROMOSUCCINIMIDE; OXAZOLINE DERIVATIVE; SPIRO COMPOUND;

EID: 9644276845     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.09.037     Document Type: Article
Times cited : (40)

References (39)
  • 11
    • 3242857105 scopus 로고
    • Review of bis(oxazoline) ligands for asymmetric catalysis: A. Pfaltz Acc. Chem. Res. 26 1993 339
    • (1993) Acc. Chem. Res. , vol.26 , pp. 339
    • Pfaltz, A.1
  • 32
    • 9644305561 scopus 로고    scopus 로고
    • note
    • The direct conversion of 5 to 4 via the corresponding dialdehyde resulted in a low yield of 4
  • 33
    • 9644298691 scopus 로고    scopus 로고
    • note
    • 3, Z = 4, R = 0.037, Rw = 0.021
  • 34
    • 9644286874 scopus 로고    scopus 로고
    • note
    • 3
  • 38
    • 9644309938 scopus 로고    scopus 로고
    • note
    • 4 and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane = 1:8) to afford the product in 62% yield with 84% ee. The enantiomeric excess of the products was determined by HPLC analysis using a chiral stationary phase column (Daicel Chiralpak AS, hexane/i-PrOH = 9:1, flow rate = 0.5 mL/min)
  • 39
    • 0142040727 scopus 로고    scopus 로고
    • 2O (0.05 mmol) in EtOH (1.5 mL) was stirred at rt for 1 h. To the resulting clear blue solution was added nitromethane (10 mmol) and p-nitrobenzaldehyde (1.0 mmol). After stirring for a further 24 h at rt, the volatile components were removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane = 1:8) to afford the product in 98% yield with 65% ee. The enantiomeric excess of the products was determined by HPLC analysis using a chiral stationary phase column (Daicel Chiralcel OD-H, hexane/i-PrOH = 9:1, flow rate = 1.0 mL/min). The product was identical in all respects to the spectra reported by Evans et al., D.A. Evans, D. Seidel, M. Rueping, H.W. Lam, J.T. Shaw, and C.W. Downey J. Am. Chem. Soc. 125 2003 12692
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12692
    • Evans, D.A.1    Seidel, D.2    Rueping, M.3    Lam, H.W.4    Shaw, J.T.5    Downey, C.W.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.