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

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

doi:10.1021/acs.orglett.9b03662

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

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

Authors

Ijaz Khan¹, Babar Hussain Shah¹, Can Zhao¹, Feng Xu², Yong Jian Zhang¹

Affiliations

¹ 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.
² Shanghai Jiao Tong University Affiliated Sixth People's Hospital South Campus , 6600 Nanfeng Highway , Shanghai 201400 , P.R. China.

PMID: 31702930
DOI: 10.1021/acs.orglett.9b03662

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 Pd₂(dba)₃·CHCl₃ and phosphoramidite L1 or L3 as a ligand under mild reaction conditions, the process afforded imidazolidinones and tetrahydropyrimidinones with high yields and high levels of enantioselectivities.