Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand

Tetrahedron Letters

Volumn 49, Issue 40, 2008, Pages 5813-5815

  Miura, Tsuyoshi ^a   Itoh, Keisuke ^a   Yasaku, Yumi ^a   Koyata, Naka ^a   Murakami, Yasuoki ^a   Imai, Nobuyuki ^a  

^a CHIBA INSTITUTE OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOPROPYLMETHANOL DERIVATIVE; FLUOROUS DISULFONAMIDE; METHANOL DERIVATIVE; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOPROPANATION; ENANTIOSELECTIVITY; SOLID PHASE EXTRACTION; SUBSTITUTION REACTION;

EID: 49549083485     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.125     Document Type: Article

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24. +: 881.0982, found: 881.0981.
25. 2 (121 μL, 1.50 mmol) at -40 °C under an argon atmosphere. The reaction mixture was stirred at 0 °C for 2.5 h, and quenched with 0.3 mL of triethylamine. The reaction mixture was extracted three times with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was chromatographed on fluorous silica gel with 70% methanol to afford 71.0 mg of a crude product. Then, the fluorous silica gel was eluted with a 1:1 mixture of methanol and ethyl acetate, and the fraction was evaporated to recover the fluorous ligand 3 (81.7 mg, 95%). The crude product was purified by column chromatography on silica gel with a 2:1 mixture of hexane and ethyl acetate to afford the pure 11a (68.9 mg, 93%) as a colorless oil.