Synthesis of Chiral Aminocyclopropanes by Rare-Earth-Metal-Catalyzed Cyclopropene Hydroamination

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• 作者：Dr. Huai-Long Teng ; Dr. Yong Luo ; Dr. Baoli Wang ; Dr. Liang Zhang ; Dr. Masayoshi Nishiura and Prof. Dr. Zhaomin Hou
• 刊名：Angewandte Chemie
• 出版年：2016
• 出版时间：December 5, 2016
• 年：2016
• 卷：128
• 期：49
• 页码：15632-15636
• 全文大小：821K
• ISSN：1521-3757

文摘

The search for efficient and selective routes for the synthesis of chiral aminocyclopropane derivatives is of great interest and importance as these structures are important components of biologically active natural products and pharmaceuticals. We herein report the enantioselective intermolecular hydroamination of substituted cyclopropenes with various amines catalyzed by chiral half-sandwich rare-earth-metal complexes. This method constitutes a 100 % atom-efficient route for the synthesis of a variety of chiral α-aminocyclopropane derivatives in high yields (up to 96 %) and excellent stereoselectivity (up to >20:1 d.r. and 99 % ee) under mild reaction conditions (25 °C).