アミドカルボニル化反応を用いる<I>N</I>-アシル-α-アミノ酸の合成
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概要
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A variety of <I>N</I>acyl-α-amino acids are synthesized from aldehyde and amide via cobalt catalyzed amido-carbonylation (Wakamatsu) reaction. The reaction proceeds under exactly the same conditions as used for the hydroformylation (Oxo) reaction. So, olefins, alcohols, epoxides and halides which give aldehydes under the reaction conditions can be satisfactorily used instead of aldehydes. When acetals are used as starting materials, <I>N</I>-acyl-α-amino esters are obtained. The intramolecular amido-carbonylation provides a convenient route to cyclic α-amino acids or esters. Furthermore, <I>N</I>-acyl-α-amino esters are synthesized from <I>N</I>-acylamines through anodic oxidation followed by amido-carbonylation with high efficiency. By utilizing the methodology, a highly stereoselective synthesis of teneraic acid 14 was achieved. Possible mechanisms for these new processes are discussed in detail.
- 社団法人 有機合成化学協会の論文