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手性方酰胺作为氢键有机催化剂实现硝基烷烃对查耳酮的高对映选择性迈克尔加成。

Highly enantioselective Michael addition of nitroalkanes to chalcones using chiral squaramides as hydrogen bonding organocatalysts.

机构信息

School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China.

出版信息

Org Lett. 2010 Dec 3;12(23):5450-3. doi: 10.1021/ol102294g. Epub 2010 Nov 5.

Abstract

A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low catalyst loading under high temperature (80 °C), affording the desired R or S enantiomers of the products flexibly in high yields with excellent enantioselectivities (93-96% ee) by the appropriate choice of organocatalysts.

摘要

一系列基于瓜环酰胺的有机催化剂被简便地合成,并作为氢键有机催化剂应用于硝基烷烃与查尔酮的对映选择性迈克尔加成反应中。这些有机催化剂在高温(80°C)下以低催化剂负载量促进迈克尔加成反应,通过适当选择有机催化剂,灵活地以高收率(93-96%ee)获得产物的所需 R 或 S 对映体。

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