Practical Oppenauer (OPP) oxidation of alcohols with a modified aluminum catalyst

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2669-2672

  Ooi, Takashi ^a   Otsuka, Hidehito ^a   Miura, Tomoya ^a   Ichikawa, Hayato ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

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EID: 0012546077     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020094c     Document Type: Article

References (73)

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68. 31
69. 28
70. 3-Al (100 μL, 0.05 mmol) was added, followed by stirring for 15 min at 21 °C. Freshly distilled carveol (795 μL, 5.0 mmol) was introduced at the same temperature, and stirring was continued for an additional 30 min. Freshly distilled pivalaldehyde (652 μL, 6.0 mmol) was added at the same temperature, and the reaction solution was stirred for 1 h. Direct purification of this solution without aqueous workup by column chromatography on silica gel (1:18 ethyl acetate/hexane as an eluant) gave carvone (708 mg, 4.71 mmol: 94% yield). The ligand, 2-hydroxy-2′-(perfluorooctanesulfo-nylamino)biphenyl, can be recovered by subsequent elution with ethyl acetate.
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