Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
Org Lett. 2011 Mar 4;13(5):876-9. doi: 10.1021/ol102933q. Epub 2011 Jan 27.
A new class of chiral secondary amine organocatalyst was rationally designed as an efficient catalyst to catalyze the elusive Michael addition of aldehydes to vinyl sulfones. High yield and excellent enantioselectivities could be obtained at room temperature without having to resort to high catalyst loading, anhydrous solvents, and low temperatures. Efficient control of enamine conformation and face shielding as well as the rigid nature of the tricyclic skeleton, with an inherent chiral pocket, provide a well-organized chiral environment to effect this elusive reaction efficiently.
一类新型的手性仲胺有机催化剂被合理设计为高效催化剂，可催化醛与乙烯砜的难以捉摸的迈克尔加成反应。在室温下即可获得高产率和优异的对映选择性，而无需使用高催化剂负载量、无水溶剂和低温。烯胺构象和面向屏蔽的有效控制以及三环骨架的刚性，具有内在的手性口袋，为有效地进行这种难以捉摸的反应提供了一个组织良好的手性环境。
