In this study, we explored a method to distinguish between both enolizable regions of unsymmetrical 2,3-diketones in organocatalytic domino reactions involving nitroalkenes. The selective formation of an enamine from only one side of the molecule was made possible by the use of optically pure 2-(trifluoromethyl)pyrrolidine. This catalyst, remarkably enhancing the reaction, owes its efficacy to a unique interplay between basicity and nucleophilicity. These features caused the enolization of the substrate at the second possible site to be omitted. The approach resulted in excellent regio- diastereo- and enantioselectivity (91-99% ee) across various nitroalkenes, leading to the synthesis of novel cyclopentanone derivatives with three contiguous stereogenic center.

中文翻译：

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不对称 2,3-二酮的有机催化活化催化不对称多米诺迈克尔-亨利反应


在这项研究中，我们探索了一种在涉及硝基烯烃的有机催化多米诺反应中区分不对称 2,3-二酮的两个烯醇化区域的方法。通过使用光学纯的 2-(三氟甲基)吡咯烷，可以仅从分子的一侧选择性形成烯胺。这种催化剂显着增强了反应，其功效归功于碱性和亲核性之间独特的相互作用。这些特征导致第二个可能位点的底物烯醇化被省略。该方法对各种硝基烯烃产生了优异的区域-双对映和对映选择性（91-99% ee），从而合成了具有三个连续立体中心的新型环戊酮衍生物。