Asymmetric Construction of Spirocyclic Pyrrolidine-thia(oxa)zolidinediones via N,O-Ligand/Cu(I) Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with 5-Alkylidene Thia(oxa)zolidine-2,4-diones

Wu-Lin Yang; Fei-Fei Tang; Fu-Sheng He; Chun-Yan Li; Xingxin Yu; Wei-Ping Deng

doi:10.1021/acs.orglett.5b02387

Asymmetric Construction of Spirocyclic Pyrrolidine-thia(oxa)zolidinediones via N,O-Ligand/Cu(I) Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with 5-Alkylidene Thia(oxa)zolidine-2,4-diones

Org Lett. 2015 Oct 2;17(19):4822-5. doi: 10.1021/acs.orglett.5b02387.

Authors

Wu-Lin Yang¹, Fei-Fei Tang¹, Fu-Sheng He¹, Chun-Yan Li¹, Xingxin Yu¹, Wei-Ping Deng¹

Affiliation

¹ School of Pharmacy and Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, P. R. China.

PMID: 26402314
DOI: 10.1021/acs.orglett.5b02387

Abstract

A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to 5-alkylidene thia(oxa)zolidine-2,4-diones catalyzed by a chiral N,O-ligand/Cu(CH3CN)4BF4 system is reported, affording structurally novel spirocyclic pyrrolidine-thia(oxa)zolidinediones with a spiro-heteroquaternary stereogenic center in good to excellent yields (up to 99%), with excellent levels of diastereo- and enantioselectivity (dr up to 99:1; ee up to 98%).

Publication types

Research Support, Non-U.S. Gov't