Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
J Org Chem. 2012 Apr 20;77(8):4136-42. doi: 10.1021/jo3001047. Epub 2012 Mar 29.
A simple chiral diamine catalyst (1a) was successfully applied in the asymmetric Michael reaction between cyclic dimedone and α,β-unsaturated ketones. Both acyclic enones with aryl or alkyl β-substituents and cyclic enones were tolerated well in the reaction. The desired adducts were obtained in high yields (up to 98%) with excellent enantioselectivities (up to 97% ee). The additives were found to increase the reactivity dramatically. The biologically active 2,4-disubstituted polyhydroquinoline scaffold was conveniently prepared through an ammoniation from the generated 3,4-dihydropyran product.
一种简单的手性二胺催化剂（1a）成功地应用于环状二酮和α，β-不饱和酮之间的不对称迈克尔加成反应。非环烯酮具有芳基或烷基β取代基和环状烯酮在反应中都能很好地被容忍。所需的加合物以高收率（高达 98%）和优异的对映选择性（高达 97%ee）获得。添加剂被发现显著提高了反应活性。通过从生成的 3,4-二氢吡喃产物氨化，方便地制备了具有生物活性的 2,4-二取代的多氢喹啉支架。
