Efficient enantioselective [3+2] cycloadditions of aldehydes and alkynes with oxiranes via selective C–C bond cleavage of epoxides were realized by chiral N,N’-dioxide L-PiPr2/Gd(III) complex and L-PyPr3/Ni(II) complex,1 respectively. The corresponding chiral 1,3-dioxolanes were obtained in up to 99% yield with up to &gt;95 : 5 dr and up to 91% ee,2 as well as a number of optically active 2,5-dihydrofurans were obtained in up to 99% yield and up to 95% ee under mild reaction conditions. 3 References： 1. Liu, X. H.; Lin, L. L.; Feng, X. M. Acc. Chem. Res. 2011, 44, 574. 2. Chen, W. L.; Lin, L. L.; Cai, Y. F.; Xia, Y.; Cao, W. D.; Liu, X. H.; Feng, X. M. Chem. Commun., 2014, 50, 2161--2163. 3. Chen, W. L.; Fu, X.; Lin, L. L.; Yuan, X.; Luo, W. W.; Feng, J. H.; Liu, X. H.; Feng, X. M., Chem. Commun., 2014, 50, 11480—11483.

Catalytic asymmetric [3 + 2] cycloadditions about oxiranes by C–C bond cleavage of epoxides

249th National Meeting (2015)

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