Stereospecific and stereoselective reactions. V. Alkylation of active methylene compounds by the use of alcohols, diethyl azodicarboxylate, and triphenylphosphine.

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概要

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• The reagent formed by the reaction of diethyl azodicarboxylate (<B>1</B>) and triphenylphosphine (<B>2</B>) reacted with alcohols and ethyl cyanoacetate (<B>6</B>) to give alkylated products in 30–80% yields. When ethyl acetoacetate, 1,3-cyclopentanedione, or 1,3-cyclohexanedione was used in place of <B>6</B>, the corresponding <I>O</I>-alkylated products were obtained. The reaction of either (<I>S</I>)-(−)-ethyl lactate or (<I>S</I>)-(−)-ethyl 2-hydroxy-3-phenylpropionate with <B>1</B>, <B>2</B>, and <B>6</B>, followed by hydrolysis resulted in the formation of (<I>S</I>)-(−)-methylsuccinic acid or (<I>S</I>)-(−)-benzylsuccinic acid. The results indicate that nearly complete inversion of the configuration takes place in the alkylation step.

• 公益社団法人 日本化学会の論文

著者

• Kurihara Toshio

  Department Of Cardiovascular Surgery Heart Institute Of Japan

• Wada Makoto

  Department Of Chemistry Faculty Of Integrated Arts And Sciences The University Of Tokushima

• Mitsunobu Oyo

  Department Of Chemistry College Of Science And Engineering Aoyama Gakuin University

• Sugizaki Masaru

  Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University

• Kime Itaru

  Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University

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