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Merging of Palladium and Organocatalysis Enabled Asymmetric Decarboxylative (2+1) Cycloadditions toward Cyclopropanes
Organic Letters ( IF 5.2 ) Pub Date : 2024-05-10 , DOI: 10.1021/acs.orglett.4c01088
Biwei Yan 1 , Pengchen Ma 2 , Xiao Shu 1 , Wenhao Yin 1 , Wusheng Guo 1
Affiliation  

A cascade reaction enabling enantio- and diastereoselective construction of strained cyclopropanes is described. This asymmetric (2+1) annulation process uses vinyl methylene carbonate and 2-cyanoacrylate as reaction partners in the presence of Pd(PPh3)4 as a precatalyst and an enantioenriched phosphoramidite ligand featuring a morpholine functionality. Mechanistic investigations unveil that the PPh3 derived from the Pd(PPh3)4 and the morpholine-containing phosphoramidite work as cooperative phosphorus and Brønsted base catalysts to promote the reaction.

中文翻译:


钯和有机催化的合并实现了环丙烷的不对称脱羧 (2+1) 环加成



描述了能够对映和非对映选择性构建应变环丙烷的级联反应。这种不对称 (2+1) 成环过程使用乙烯基亚甲基碳酸酯和 2-氰基丙烯酸酯作为反应伙伴,并在 Pd(PPh 3 ) 4 作为预催化剂和对映体富集的亚磷酰胺配体存在下具有吗啉功能。机理研究表明,由 Pd(PPh 3 ) 4 衍生的 PPh 3 和含吗啉的亚磷酰胺作为协同磷和布朗斯台德碱催化剂,促进的反应。
更新日期:2024-05-10
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