新型手性辅剂N-甲基苯丙胺醇诱导不对称Michael加成反应研究  

Study on Asymmetric Michael Addition Induced by Novel Chiral Adjuvant N-methamphetamine

作　　者：云惟贤 许园 陈燕 杨杰 庞朝海 Yun Weixian;Xu Yuan;Chen Yan;Yang Jie;Pang Chaohai(Analysis and Test Center,Chinese Academy of Tropical Agricultural Sciences,Hainan Provincial Key Laboratory of Quality and Safety for Tropical Fruits and Vegetables,Haikou 571101;Hainan Haiyao Co.,Ltd.,Haikou 570311;Key Laboratory of Tropical Translational Medicine of Ministry of Education,School of Pharmacy,Hainan Medical University,Haikou 571199,China)

机构地区：[1]中国热带农业科学院分析测试中心,海南省热带果蔬产品质量安全重点实验室,海南海口571101 [2]海南海药股份有限公司,海南海口570311 [3]海南医学院药学院,热带转化医学教育部重点实验室,海南海口571199

出　　处：《广东化工》2023年第6期8-9,62,共3页Guangdong Chemical Industry

基　　金：海南省自然科学基金项目(320QN302)。

摘　　要：新型手性辅助剂是Michael加成反应体系中一类重要的催化剂,可实现高立体选择性的Michael加成反应。本论文以苯丙氨酸制备的手性N-甲基苯丙胺醇作为手性辅剂,通过其与溴代芳基醛形成四氢噁唑芳基锂试剂,然后对烷基的α,β-不饱和叔丁酯类化合物(1-环戊烯甲酸叔丁酯和1-环己烯甲酸叔丁酯受体)进行了不对称共轭加成反应研究。本方法成功制备了ee值为90%~95%和产率为35%~55%的加成产物(6/7/6a/6b/7a/7b)。The novel chiral auxiliary is an important type of catalysts in the Michael addition reaction system,which can realize the Michael addition reaction with high stereoselectivity.In this research,starting from chiral auxiliary N-methyl-phenylalaninol,four oxazole aryl lithium reagents were synthesized,and then studies on the asymmetric conjugate addition reaction with differentα,β-unsaturated tert-butyl ester compounds were conducted.This technique successfully prepared addition products with ee values of 90%~95%and yields of 35%~55%(6/7/6a/6b/7a/7b).

关 键 词：MICHAEL加成反应 立体选择性 不对称共轭加成 手型辅剂 合成 

分 类 号：TQ[化学工程]