Zhang Lili, Liu Yang, Liu Kun, Liu Zhantao, He Ningning, Li Wenjun
Department of Medicinal Chemistry, School of Pharmacy, Qingdao University, Qingdao, 266021, China.
Org Biomol Chem. 2017 Oct 25;15(41):8743-8747. doi: 10.1039/c7ob02325a.
Enantioselective organocatalytic inverse-electron-demand hetero-Diels-Alder reactions of in situ generated ortho-quinone methides with azlactones have been developed. This strategy could generate various chiral dihydrocoumarins bearing a quaternary amino acid moiety in high yields (up to 94%) and stereoselectivities (up to 99 : 1 e.r., >20 : 1 dr) in the presence of a chiral phosphoric acid catalyst. The useful transformation and mechanistic study of this process are also presented.
已开发出原位生成的邻醌甲基化物与恶唑酮的对映选择性有机催化反电子需求杂Diels-Alder反应。在 chiral磷酸催化剂存在下，该策略可以高产率（高达94%）和立体选择性（高达99:1的对映体过量，>20:1的非对映体比例）生成各种带有季氨基酸部分的手性二氢香豆素。还介绍了该过程的有用转化和机理研究。
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