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. 2015 Oct 2;17(19):4822-5.
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

Wu-Lin Yang  1 , Fei-Fei Tang  1 , Fu-Sheng He  1 , Chun-Yan Li  1 , Xingxin Yu  1 , Wei-Ping Deng  1
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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 et al. Org Lett. .

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%).

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