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钯催化含氮烯丙基碳酸酯与异氰酸酯的不对称烯丙基环加成反应

Pd-Catalyzed Asymmetric Allylic Cycloaddition of N-Containing Allylic Carbonates with Isocyanates.

作者信息

Khan Ijaz, Shah Babar Hussain, Zhao Can, Xu Feng, Zhang Yong Jian

机构信息

School of Chemistry and Chemical Engineering, and Shanghai Key Laboratory of Electrical Insulation and Thermal Aging , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , P.R. China.

Shanghai Jiao Tong University Affiliated Sixth People's Hospital South Campus , 6600 Nanfeng Highway , Shanghai 201400 , P.R. China.

出版信息

Org Lett. 2019 Dec 6;21(23):9452-9456. doi: 10.1021/acs.orglett.9b03662. Epub 2019 Nov 8.

Abstract

An efficient method for the enantioselective synthesis of cyclic ureas has been developed through Pd-catalyzed asymmetric allylic cycloaddition of readily accessible nitrogen-containing allylic carbonates with isocyanates. By using a palladium complex in situ generated from Pd(dba)·CHCl and phosphoramidite or as a ligand under mild reaction conditions, the process afforded imidazolidinones and tetrahydropyrimidinones with high yields and high levels of enantioselectivities.

摘要

通过钯催化易得的含氮烯丙基碳酸酯与异氰酸酯的不对称烯丙基环加成反应,开发了一种对映选择性合成环状脲的有效方法。在温和的反应条件下,使用由Pd(dba)·CHCl和亚磷酰胺原位生成的钯配合物或作为配体,该过程以高收率和高对映选择性得到咪唑烷酮和四氢嘧啶酮。

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