Stereospecific and Stereoselective Reactions. II. Preparation of Esters of <I>N</I>-Phthaloyl-α-amino Acid from Esters of α-Hydroxy Acid
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概要
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Functional selectivity and stereospecificity of the intermolecular dehydration between alcohols and phthalimide (III) by means of diethyl azodicarboxylate (I) and triphenylphosphine (II) was examined. The reaction of allyl alcohol, 2-chloroethanol or (±)-ethyl lactate with I, II, and III led to the formation of corresponding <I>N</I>-alkylphthalimide. The reaction was further applied to the synthesis of esters of <I>N</I>-phthaloyl-α-amino acid. (<I>S</I>)-(−)-ethyl 2-hydroxy-3-phenylpropionate was converted into (<I>R</I>)-(+)-<I>N</I>-phthaloylphenylalanine ethyl ester with high stereospecificity.
- 公益社団法人 日本化学会の論文
著者
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Wada Makoto
Department Of Chemistry Faculty Of Integrated Arts And Sciences The University Of Tokushima
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Mitsunobu Oyo
Department Of Chemistry College Of Science And Engineering Aoyama Gakuin University
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Sano Takashi
Department Of Biochemistry And Medicine School Of Medicine And Nursing Kitasato University
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