Institute of Microbial Chemistry (BIKAKEN), Tokyo (Japan), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan).
Angew Chem Int Ed Engl. 2015 Apr 20;54(17):5183-6. doi: 10.1002/anie.201412377. Epub 2015 Mar 3.
Optically active vicinal diamines are versatile chiral building blocks in organic synthesis. A soft Lewis acid/hard Brønsted base cooperative catalyst allows for an efficient stereoselective coupling of N-alkylidene-α-aminoacetonitrile and ketimines to access this class of compounds bearing consecutive tetra- and trisubstituted stereogenic centers. The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as 3 mol % catalyst loading.
手性光学活性邻二胺是有机合成中用途广泛的手性砌块。一种软路易斯酸/硬布朗斯台德碱协同催化剂可以有效地立体选择性地偶联 N-亚烷基-α-氨基乙腈和亚胺，从而获得这类含有连续四个和三个取代立体中心的化合物。在亚胺中战略性地使用软路易斯碱性硫代膦酰基是促进反应的关键，而脂肪族亚胺可以在低至 3 mol%的催化剂负载量下作为合适的底物。
