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Volumn , Issue 14, 2007, Pages 2193-2196

Asymmetric organozincate additions to ethyl 2,2,2-trifluoropyruvate

Author keywords

keto ester; Asymmetric organometallic addition; BINOL; Trifluoropyruvate; Zincate

Indexed keywords

ALPHA TRIFLUOROMETHYL ALPHA HYDROXY ACID; ETHYL 2,2,2 TRIFLUOROPYRUVIC ACID; HYDROXYACID; ORGANOZINCATE; PYRUVIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

EID: 34548736485     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984911     Document Type: Article
Times cited : (21)

References (27)
  • 15
    • 0035830539 scopus 로고    scopus 로고
    • Enantioselective Friedel-Crafts reaction with ethyl 2,2,2- trifluoropyruvate: (a) Zhuang, W.; Gatherwood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009.
    • Enantioselective Friedel-Crafts reaction with ethyl 2,2,2- trifluoropyruvate: (a) Zhuang, W.; Gatherwood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009.
  • 18
    • 0742287187 scopus 로고    scopus 로고
    • Enantioselective carbonyl-ene reaction: Aikawa, K.; Kainuma, S.; Manabu, H.; Mikami, K. Tetrahedron Lett. 2004, 45, 183.
    • (d) Enantioselective carbonyl-ene reaction: Aikawa, K.; Kainuma, S.; Manabu, H.; Mikami, K. Tetrahedron Lett. 2004, 45, 183.
  • 19
    • 34548808040 scopus 로고    scopus 로고
    • 19F NMR spectroscopic analysis with benzotrifluoride as internal standard (δ = -61.5 ppm).
    • 19F NMR spectroscopic analysis with benzotrifluoride as internal standard (δ = -61.5 ppm).
  • 24
    • 17244369977 scopus 로고    scopus 로고
    • For reviews on the use of BINOL in asymmetric synthesis, see: a
    • For reviews on the use of BINOL in asymmetric synthesis, see: (a) Brunei, J. M. Chem. Rev. 2005, 105, 857.
    • (2005) Chem. Rev , vol.105 , pp. 857
    • Brunei, J.M.1
  • 26
    • 23944434907 scopus 로고    scopus 로고
    • A similar BINOL-derived zincate species has been reported as a Lewis acid catalyst for enantioselective Diels-Alder cycloadditions: Ward, D. E, Souweha, M. S. Org. Lett. 2005, 7, 3533
    • A similar BINOL-derived zincate species has been reported as a Lewis acid catalyst for enantioselective Diels-Alder cycloadditions: Ward, D. E.; Souweha, M. S. Org. Lett. 2005, 7, 3533.
  • 27
    • 34548745196 scopus 로고    scopus 로고
    • Experimental Procedure (R, )-1,1′-Bi(2-naphthol)(5. 1 g, 17.6 mmol, 120 mol, was dissolved in anhyd 1,2-dichloroethane (35 mL) and THF (8.75 mL) and the solution was cooled to -40°C. A solution of Et 2Zn (13.4 mL, 14.7 mmol, 100 mol, 1.1 M in toluene) was added over 30 min. Caution: gas evolution! Proper venting required! The mixture was stirred at r.t. for 1 h, cooled to -40°C and a solution of EtMgCl (8.8 mL, 17.6 mmol, 120 mol, 2 M in THF) was added over 15 min. The solution was warmed to r.t. for 1 h and then cooled to -40°C. Ethyl 2,2,2-trifluoropyruvate (1.95 mL, 2.50 g, 14.7 mmol) was added dropwise via syringe pump over 6 h. The mixture was let stir 18 h and then quenched with 2 N aq HCl (25 mL, The organic layer was washed with 1 N aq NaOH (3 x 20 mL, The organic layer was then treated with 8 N KOH 200 mol, at reflux for 2 h. The solution was cooled to r.t. and the layers were separated. The aqueous layer was washed wi
    • 3 at -61.5 ppm): δ = -77.3. Chiral GC analysis (methyl ester): Cyclodex-B column, 50°C for 1 min, 5°C/min to 95°C, hold at 95°C for 1 min, 20°C/min to 200°C, injector 180°C, detector 250°C, split 10:1, 13.5 psi He, S-enantiomer at 6.10 min, R-enantiomer at 6.83 min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.