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Volumn 76, Issue 2, 2008, Pages 995-1000

Kinetic resolution of 1,2-diols using nitrogen-tethered bisimidazoline-copper(I) catalyzed benzoylation

Author keywords

1,2 Diol; Asymmetric Catalyst; Benzoylation; Imidazoline; Kinetic Resolution

Indexed keywords


EID: 61349175955     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(N)59     Document Type: Article
Times cited : (6)

References (27)
  • 24
    • 61349157126 scopus 로고    scopus 로고
    • Typical experimental procedure (Table 2, entry 3, Nb-imidazoline (7.3 mg, 8.25μmol) and CuCl (0.74 mg, 7.5 μmol) were stirred for 3 h at rt in CH2Cl2(1.5 mL) under Ar atmosphere. To the solution were added 1,2-butanediol (11 μL, 0.15 mmol, i-Pr2NEt (25.7 μL, 0.15 mmol, and o-methylbenzoyl chloride (9.7 μL, 0.075 mmol) at -40 °C. After stirring for 20 h, the solution was poured onto water and the aqueous layer was extracted with CHCl3 (10 mL x 3, The combined organic extracts were dried over anhydrous Na2SO4 and concentrated in vacuo after filtration. The residual crude product was purified by silica gel chromatography (hexane:EtOAc, 3:1) to give the product. The ee of the adduct was determined by chiral stationary phase HPLC analysis Daicel Chiralpak AS-H
    • 4 and concentrated in vacuo after filtration. The residual crude product was purified by silica gel chromatography (hexane:EtOAc = 3:1) to give the product. The ee of the adduct was determined by chiral stationary phase HPLC analysis (Daicel Chiralpak AS-H).
  • 25
    • 61349183581 scopus 로고    scopus 로고
    • In the reaction using pheny-1,2-ethanediol, when the major secondary alcohol 1 was obtained in 36% yield with 54% ee and the minor primary alcohol 2 was obtained in 7% yield with 73% ee, the (S)-enriched starting diol was recovered in 41% with 29% ee
    • In the reaction using pheny-1,2-ethanediol, when the major secondary alcohol 1 was obtained in 36% yield with 54% ee and the minor primary alcohol 2 was obtained in 7% yield with 73% ee, the (S)-enriched starting diol was recovered in 41% with 29% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.