Stereoselective reduction of ketones by various vegetables |
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Authors: | Takamitsu Utsukihara Satoshi Watanabe Atsushi Tomiyama Wen Chai C. Akira Horiuchi |
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Affiliation: | aDepartment of Chemistry, Rikkyo (St. Paul's) University, Nishi-Ikebukuro, Toshima-Ku, Tokyo 171-8501, Japan bDepartment of Chemistry, Changshu Institute of Technology, Changshu 215500, PR China |
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Abstract: | Reduction of (+)-and (−)-camphorquinones (1a, 1b) by various vegetables (carrot, potato, sweet potato, apple, Japanese radish, cucumber, burdock and onion) gave -hydroxycamphor selectively. Using burdock, (+)-camphorquinone was reduced to give (−)-3S-exo-hydroxycamphor (4a) as major product in high stereoselectivity with high yield. Moreover, 1,2-cyclohexanedione (1c) and 2-methylcyclohexanone (1d) with various vegetables afford enantiomerically pure trans- and/or cis-alcohol, respectively. Various vegetable reduction gave a new idea of a biotechnological process. |
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Keywords: | Vegetable Stereoselectivity (+)- and (−)-Camphorquinone 1,2-Cyclohexanedione 2-Methylcyclohexanone |
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