Substiuent effect on the enantiomer-differentiating reaction of lithiomethyl p-total sulfoxide with meta- or para-substituted(R)-(-)-menthyl benzoates.

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概要

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• Treatment of (<I>R</I>)-(−)-menthyl benzoates, which have a variety of meta- or para-substituents, with 2 equivalents of racemic lithiomethyl <I>p</I>-tolyl sulfoxide displays the feature of an enantiomer-differentiating reaction, affording the corresponding optically active β-keto sulfoxides. The degree and the direction of enantioselectivity were affected by the nature of the substituent on benzene ring. The electron-releasing substituents trend to increase the %e.e. value. The reversal in the configuration with the variation in the substituent which has a high electron-withdrawing <I>p</I>-CN group was also observed. The <I>R</I>⁄<I>S</I> values thus obtained gave a good correlation with Hammett's a values (<I>r</I>=0.975), affording a negative straight line. Based on these observations, a plausible stereochemical course of this reaction has been discussed.

• 公益社団法人 日本化学会の論文

著者

• Kinoshita Masayoshi

  Department Of Bioapplied Chemistry Faculty Of Engineering Osaka City University

• KUNIEDA Norio

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

• Nakanishi Takeshi

  Department Of Applied And Bioapplied Chemistry Graduate School Of Engineering Osaka City University

• Kunieda Norio

  Department Of Applied Chemistry Faculty Of Engineering Osaka City University

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