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Lithium phenoxide-catalyzed asymmetric synthesis

Lithium alkoxide is a typical base and is used in various reactions, but in the presence of water it decomposes into lithium hydroxide and alcohol. On the other hand, lithium phenoxide is a stable base even in water because it is around pKa10 of phenol. Binaftor is one of the representative optically active phenol derivatives, but its lithium salt, lithium binaphtholate, has surprisingly been rarely used as an asymmetric catalyst. In our laboratory, we found that the introduction of a substituent at the 3,3'position of lithium vinaftrat functions as an extremely effective asymmetric catalyst.

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