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Volumn , Issue 3, 2007, Pages 435-438

Copper-catalyzed kinetic resolution of 1,3-cyclohexadiene monoepoxide with grignard reagents

Author keywords

Asymmetric synthesis; Catalysis; Copper; Epoxides; Grignard reagents

Indexed keywords

1,3 CYXLOHEXADINE MONOEPOXIDE; COPPER; EPOXIDE; FERROCENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847372041     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967945     Document Type: Article
Times cited : (19)

References (16)
  • 1
    • 0004246896 scopus 로고    scopus 로고
    • Krause, N, Ed, Wiley-VCH: Weinheim
    • Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002.
    • (2002) Modern Organocopper Chemistry
  • 3
    • 3042822552 scopus 로고    scopus 로고
    • For a review see
    • (b) For a review see: Pineschi, M. New J. Chem. 2004, 28, 657.
    • (2004) New J. Chem , vol.28 , pp. 657
    • Pineschi, M.1
  • 14
    • 33847385811 scopus 로고    scopus 로고
    • 3, whereas MTBE has to be distilled over Na/benzophenone.
    • 3, whereas MTBE has to be distilled over Na/benzophenone.
  • 15
    • 33847401863 scopus 로고    scopus 로고
    • Typical Procedure: In a dried Schlenk tube under N2 atmosphere were placed CuBr (1.4 mg, 0.01 mmol) and (R,S)-L11 (7.0 mg, 0.011 mmol, Et2O was added (6 mL) and the mixture was stirred at r.t. for 20 min. The tube was cooled to -78°C and 1,3-cyclohexadiene monoepoxide (1; 100 μL, 1 mmol) was added. BuMgCl (250 μL, 2.0 M in Et2O, 0.5 mmol) was added dropwise over a period of 3 min. The reaction was stirred for 1 h and quenched with MeOH and (NH4) 2SO4 before being allowed to reach r.t. The aqueous phase was extracted with Et2O and the organic layers were dried over Na2SO4 and the solvent was removed on a rotary evaporator (45% conversion, 90% ee, The crude was poured in Ac2O (1 mL, 10 mmol) in the presence of Et3N (100 μL) and DMAP (a few mg, The mixture was stirred overnight at r.t. The reaction was quenched with MeOH 100
    • 3, ee = 90%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.