Promiscuous acylase-catalyzed aza-Michael additions of aromatic N-heterocycles in organic solvent

作者：Qian, Chao; Xu, Jian-Ming; Wu, Qi; Lv, De-Shui; Lin, Xian-Fu^*

来源：Tetrahedron Letters, 2007, 48(35): 6100-6104.

DOI：10.1016/j.tetlet.2007.06.164

• ALPHA,BETA-ETHYLENIC COMPOUNDS
• CONJUGATE ADDITION
• ALKALINE PROTEASE
• BACILLUS-SUBTILIS
• ALIPHATIC-AMINES
• SYSTEM
• WATER
• DERIVATIVES
• ACTIVATION
• INHIBITORS

A novel and efficient enzymatic promiscuous protocol for aza-Michael addition of aromatic N-heterocycles to alpha,beta-unsaturated compounds has been described. The reactions were catalyzed by promiscuous zinc-active-site acylase in organic solvent at 50 degrees C. The strategy works with a broad range of N-heterocycles to afford the corresponding Michael adduct with good yields in several hours (0.5-6 h). This catalytic promiscuity is the first example of metal-active-site enzyme-catalyzed aza-Michael addition for aromatic N-heterocycles.

• 出版日期2007-8-27
• 单位浙江大学