Enantioselective iridium-catalyzed hydrogenation of α-arylcinnamic acids and?synthesis of (S)-equol

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• 作者：Shuang Yang ; Shou-Fei Zhu ; Can-Ming Zhang ; Song Song ; Yan-Bo Yu ; Shen Li ; Qi-Lin Zhou ; ^{qlzhou@nankai.edu.cn}
• 关键词：Asymmetric catalysis ; Hydrogenation ; Chiral spiro ligands ; 伪-Arylcinnamic acids ; (S)-Equol
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：1 July, 2012
• 卷：68
• 期：26
• 页码：5172-5178
• 文件大小：462 K

摘要

By using iridium catalyst based on chiral spiro phosphine-oxazoline ligands, the hydrogenation of α-arylcinnamic acids was accomplished under ambient pressure and low catalyst loading (as low as 0.01?mol?%), providing useful 2,3-diarylpropionic acids in high yields with excellent enantioselectivities (up to 99%ee). A catalytic enantioselective synthesis of (S)-equol with the present hydrogenation reaction as a key step was accomplished starting from commercially available starting materials in six steps with 48.4%overall yield.