School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, PR China.
Org Biomol Chem. 2012 Apr 14;10(14):2840-6. doi: 10.1039/c2ob00003b. Epub 2012 Mar 2.
Perhydroindolic acids, the by-products obtained in the industrial production of a trandolapril intermediate, were used as chiral organocatalysts in asymmetric Michael addition reactions of aldehydes to nitroolefins. These proline-like catalysts are unique for their rigid bicyclic structure with two H atoms attached to the bridgehead C atoms lying on the opposite side of the ring. They therefore showed high efficiency in asymmetric Michael additions of aldehydes to nitroolefins. Under the optimal conditions, excellent diastereo- and enantioselectivities (up to 99/1 dr and 98% ee) were obtained with high chemical yields for a series of aldehydes and nitroolefins using only 5 mol% catalyst loading. The methodology features easily available catalysts, high catalytic efficiency and environmentally green procedures.
在反式哒嗪普利中间体的工业生产中获得的氢过吲哚酸被用作手性有机催化剂，用于醛与硝基烯烃的不对称迈克尔加成反应。这些脯氨酸类似的催化剂因其刚性双环结构而独特，两个 H 原子连接到桥接碳原子上，位于环的对面。因此，它们在醛与硝基烯烃的不对称迈克尔加成反应中表现出高效性。在最佳条件下，仅使用 5 mol%的催化剂负载量，即可使用一系列醛和硝基烯烃获得优异的非对映选择性和对映选择性（高达 99/1 dr 和 98%ee）和高化学收率。该方法的特点是使用易于获得的催化剂、高催化效率和环境友好的程序。
