Zhu Fang, Shen Qi-Wen, Wang Wen-Zhe, Wu Zhu-Lian, Cai Tian, Wen Wei, Guo Qi-Xiang
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
Org Lett. 2021 Feb 19;23(4):1463-1467. doi: 10.1021/acs.orglett.1c00143. Epub 2021 Feb 5.
A ternary catalytic system comprising a chiral aldehyde, a transition metal, and a Lewis acid is rationally designed for the asymmetric α-allylic alkylation reaction of aza-aryl methylamines and π-allylmetal electrophiles. Structural diversity chiral amines bearing carbon-carbon double bonds and aza-heterocycles are produced in moderate to good yields with good to excellent enantioselectivities. These products can be readily converted into other chiral amines without the loss of enantioselectivity. A reasonable reaction mechanism is proposed to illustrate the stereoselective control results.
合理设计了一种由手性醛、过渡金属和路易斯酸组成的三元催化体系,用于氮杂芳基甲胺与π-烯丙基金属亲电试剂的不对称α-烯丙基烷基化反应。生成了带有碳-碳双键和氮杂环的结构多样的手性胺,产率中等至良好,对映选择性良好至优异。这些产物可以很容易地转化为其他手性胺,而不会损失对映选择性。提出了一个合理的反应机理来解释立体选择性控制结果。