Diastereoselective arylation of l-proline derivatives at the 5-position

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• 作者：Osamu Onomura ; Peter G. Kirira ; Toshimitsu Tanaka ; Shinsuke Tsukada ; Yoshihiro Matsumura ; Yosuke Demizu
• 关键词：Diastereoselective ; Organocatalysis ; Asymmetric reduction of imines ; C₂-symmetrical pyrrolidine ; Proline derivative
• 刊名：Tetrahedron
• 出版年：2008
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：4 August 2008
• 卷：64
• 期：32
• 页码：7498-7503
• 文件大小：336 K

摘要

Diastereoselective introduction of nucleophiles into l-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Methoxycarbonylated or benzyloxycarbonylated l-proline derivatives reacted with arene to give cis-arylated products. On the other hand, N-benzoylated l-proline derivative preferentially gave trans-arylated product, which could be easily transformed into optically active C₂-symmetrical pyrrolidine derivative. Such derivative 5 worked well as an organic activator in the asymmetric reduction of aromatic imines by Cl₃SiH.