Zou Ning, Jiao Ji-Wen, Feng Yu, Pan Cheng-Xue, Liang Cui, Su Gui-Fa, Mo Dong-Liang
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences , Guangxi Normal University , 15 Yu Cai Road , Guilin , 541004 , China.
Org Lett. 2019 Jan 18;21(2):481-485. doi: 10.1021/acs.orglett.8b03767. Epub 2019 Jan 10.
An efficient one-pot synthesis of polysubstituted pyrrolizines from N-vinyl- α,β-unsaturated nitrones and activated alkynes through iron(III)/copper(II)-cocatalyzed [3 + 2] cycloaddition/[3,3]-rearrangement and sequential N-O bond cleavage was developed. The reaction first underwent [3 + 2] cycloaddition and [3,3]-rearrangement to afford nine-membered N-heterocycles, and then a controlled N-O bond cleavage of nine-membered rings by iron(III)/copper(II) cocatalysts delivered pyrrolizine scaffolds. A kinetic resolution of nine-membered ring compounds was achieved for the first time by using copper(II) acetate combined with a chiral PyBox ligand.
