Iron(III)/Copper(II)-Cocatalyzed Cycloaddition/[3,3]-Rearrangement/N–O Bond Cleavage To Prepare Polysubstituted Pyrrolizines from N-Vinyl-α,β-Unsaturated Nitrones and Activated Alkynes

• DOI: 10.1021/acs.orglett.8b03767
• Publication Date: 2019-01-10T15:17:25Z
• Authors: Ning Zou; Ji-Wen Jiao; Yu Feng; Cheng-Xue Pan; Cui Liang; Gui-Fa Su; Dong-Liang Mo
• Keywords: Bond cleavage; Cleavage (geology)

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 sequential N–O bond cleavage was developed. The reaction first underwent cycloaddition [3,3]-rearrangement to afford nine-membered N-heterocycles, then a controlled rings by iron(III)/copper(II) cocatalysts delivered pyrrolizine scaffolds. A kinetic resolution ring compounds achieved for the time using copper(II) acetate combined with chiral PyBox ligand.