Enantioselective borohydride reduction catalyzed by optically active cobalt complexes |
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Authors: | Yamada Tohru Nagata Takushi Sugi Kiyoaki D Yorozu Kiyotaka Ikeno Taketo Ohtsuka Yuhki Miyazaki Daichi Mukaiyama Teruaki |
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Institution: | Basic Research Laboratories for Organic Synthesis, Mitsui Petrochemical Industries Ltd., Nagaura, Sodegaura-shi, Chiba 299-0265, Japan. yamada@chem.keio.ac.jp |
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Abstract: | The highly enantioselective borohydride reduction of aromatic ketones or imines to the corresponding alcohols was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. This enantioselective reduction is carried out using a precisely premodified borohydride with alcohols such as tetrahydrofurfuryl alcohol, ethanol and methanol. High optical yields are obtained by choosing the appropriate alcohol as modifiers and a suitable beta-ketoiminato ligand of the catalyst. The enantioselective borohydride reduction has been successfully applied to the preparation of optically active 1,3-diols, the stereoselective reduction of diacylferrocenes, and dynamic and/or kinetic resolution of 1,3-dicarbonyl compounds. |
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Keywords: | asymmetric catalysis diastereoselectivity enantioselectivity kinetic resolution reduction |
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