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Volumn 7, Issue 10, 1996, Pages 2809-2812

Synthesis and applications of a new class of C2 symmetric phosphorus donor ligand for asymmetric catalysis

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL DERIVATIVE;

EID: 0030272367     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00368-0     Document Type: Article
Times cited : (27)

References (15)
  • 3
    • 0041768560 scopus 로고
    • 2) The significance of the array of four aromatic rings has been addressed in detail, for example; (a) R. Noyori, Chem. Soc. Rev., 1989, 18, 225.
    • (1989) Chem. Soc. Rev. , vol.18 , pp. 225
    • Noyori, R.1
  • 8
    • 85030270496 scopus 로고    scopus 로고
    • note
    • 4) The following are representative of the methods we attempted; 1,2-dibromoethane in THF, DMF or DMSO using sodium hydride (with and without added silver salts or 18-crown-6), butyllithium. potassium carbonate, P4 superbase; also with sodium hydride as base in THF: ethane-1,2-diol(bis)trifluorosulfonate, 1,2 diiodoethane, 1,3 dibromopropane, oxalyl chloride; ethane-1,2-diol with triphenylphosphine and DEAD.
  • 9
    • 0001767033 scopus 로고
    • 5) A sample of S-5 was generously provided by SmithKline Beecham, however for the synthesis of the antipodal diphosphine ligand it was necessary to prepare R-5 by the asymmetric reduction of o-bromoacetophenone using the method reported by Evans; D. A. Evans, S. G. Nelson, M. R. Gagne and A. R. Muci, J. Am. Chem. Soc., 1993, 115, 9800.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9800
    • Evans, D.A.1    Nelson, S.G.2    Gagne, M.R.3    Muci, A.R.4
  • 11
    • 85030268000 scopus 로고    scopus 로고
    • note
    • 7) The methine protons in 2a and 2e appear as quartets at δ4.98 and 5.52 ppm respectively. Their cis-diastereoisomers have corresponding resonances at δ4.86 and 5.08 ppm (multiplet and sextet respectively). The same pattern is repeated in a derivative of 2a containing a 2-pyrollidylethyl group in the nitrogen atom, the relative configuration in which, like 2e, has been confirmed by X-ray crystallography. Compound (SpS)(SpS)-1 displayed a quartet at δ4.63 ppm for the methine resonance.
  • 12
    • 6844254916 scopus 로고    scopus 로고
    • 8) For an excellent recent review see B. M. Trost, Chem. Rev. 1996, 96, 395.
    • (1996) Chem. Rev. , vol.96 , pp. 395
    • Trost, B.M.1
  • 14
    • 0001540849 scopus 로고
    • 10a - 10c: Chiral HPLC, Chiralcel OD column, 1.0-8% isopropanol (depending on sample) in hexane containing 0.1% diethylamine. 1-(1-Naphthyl)ethanol; chiral HPLC on Chiralcel OJ column using 8% isopropanol in hexane containing 0.1% diethylamine. Flow rates of 0.5-1ml/min give excellent separations although exact elution times and efficiency of separation depend on exact column dimensions and history. Further details will be given in a full paper. Absolute configurations confirmed for 10a to 10c and 1-(1-naphthyl)ethanol by optical rotation sign as given in ref. 5 and (a) M. B. Carter, B. Schiott, A. Gutierrez and S. L. Buchwald, J. Am. Chem. Soc., 1994, 116, 11667,
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 11667
    • Carter, M.B.1    Schiott, B.2    Gutierrez, A.3    Buchwald, S.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.