脯氨酸衍生物催化蒽酮与硝基烯烃的不对称Michael加成反应

Proline derivative organocatalyzed asymmetric michael reaction of anthrone and β-nitroalkenes

目的筛选出适用于β-硝基烯的不对称Michael加成反应的有机催化剂体系。方法设计、合成脯氨酸衍生物催化剂,应用于反式硝基苯乙烯和蒽酮的不对称Michael加成反应。考察溶剂、温度、催化剂用量等因素对反应立体选择性的影响。结果最佳的催化剂体系为:10 mol%的催化剂1b,甲苯为溶剂,室温反应。结论将筛选出的催化剂体系用于不同取代基的反式β-硝基烯烃和蒽酮的不对称Michael加成反应,得到了很好的产率(88%~98%)和最高达66%ee的立体选择性。

Objective To screen out the organiccatalyst system for the asymmetric Michael addition reaction of β-nitroene. Methods Proline Derivative as organocatalysts were applied in asymmetric Michael addition reaction of anthrone with different nitroalkenes.The effect of solvent,temperature and catalyst loading were investigated. Results The optimized conditions were confirmed to include toluene as the solvent with a 10% catalyst of 1b at room temperature. Conclusion The screened catalyst system is applied to the asymmetric Michael addition reaction of anthrone with 10 nitroalkenes,the products were obtained in 88%~98% yield and with up to 66%ee.