Palladium-Catalyzed Asymmetric (2+3) Annulation of p-Quinone Methides with Trimethylenemethanes: Enantioselective Synthesis of Functionalized Chiral Spirocyclopentyl p-Dienones
Palladium-Catalyzed Asymmetric (2+3) Annulation of p-Quinone Methides with Trimethylenemethanes: Enantioselective Synthesis of Functionalized Chiral Spirocyclopentyl p-Dienones
复制标题
钯催化对醌甲基化物与三亚甲基甲烷的不对称 (2 3) 环化：对映选择性合成官能化手性螺环戊基对二烯酮
DOI：
10.1021/acs.orglett.0c01252
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发表时间：
2020
期刊：
影响因子：
5.2
通讯作者：
Chun-An Fan
中科院分区：
文献类型：
--
作者：
Zhi-Long Jia;Xian-Tao An;Yu-Hua Deng;Hui-Bin Wang;Kang-Ji Gan;Jing Zhang;Xian-He Zhao;Chun-An Fan
描述了在钯催化下对醌甲基化物与 CN 取代的三亚甲基甲烷的新型不对称催化 (2+3) 成环反应，为高度官能化的手性螺环戊基对二烯酮的对映选择性构建提供了另一种方法。在反应活性和对映选择性显着改善的推动下，一种新型的非 C2 对称亚磷酰胺配体由 (S)-BINOL 和源自 1-羟脯氨酸的空间要求胺的手性匹配组合演化而来，并针对此处介绍的方案进行了探索。
A novel asymmetric catalytic (2+3) annulation ofp-quinone methides with CN-substituted trimethylenemethane is described under palladium catalysis, providing an alternative approach for the enantioselective construction of highly functionalized chiral spirocyclopentylp-dienones. Driven by the significant improvement in the reactivity and enantioselectivity, a novel type of non-C2-symmetric phosphoramidite ligand from the chirality-matched combination of (S)-BINOL and sterically demanding amine derived froml-hydroxyproline is evolved and explored for the protocol presented here.