Soft Molecular Activation Research Center (SMARC), Chiba Iodine Resource Innovation Center (CIRIC), Molecular Chirality Research Center (MCRC), Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Org Biomol Chem. 2021 Aug 28;19(32):6969-6973. doi: 10.1039/d1ob00796c. Epub 2021 Aug 2.
A chiral quinine-derived organic base catalyst with halogen bond donor functionality was used to catalyze the asymmetric double Mannich reaction of malononitrile with N-Boc and N-Cbz imines to afford 1,3-diamines in excellent yields with high enantio- and diastereoselectivities. With 2.2 equiv. of a single imine electrophile, symmetrical 1,3-diamines were obtained, whereas, with two different imine partners, unsymmetrically substituted 1,3-diamine was obtained. The monohydration of the double Mannich product was also achieved.
一种手性奎宁衍生的有机碱催化剂，具有卤键供体官能团，可用于催化丙二腈与 N-Boc 和 N-Cbz 亚胺的不对称双曼尼希反应，以高收率和高对映选择性和非对映选择性得到 1,3-二胺。使用 2.2 当量的单一亚胺亲电试剂，可得到对称的 1,3-二胺，而使用两个不同的亚胺配体，则可得到不对称取代的 1,3-二胺。双曼尼希产物的单水合也可以实现。
