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

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] cycload...

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Bibliographic Details
Published in:Organic letters 2019-01, Vol.21 (2), p.481-485
Main Authors: Zou, Ning, Jiao, Ji-Wen, Feng, Yu, Pan, Cheng-Xue, Liang, Cui, Su, Gui-Fa, Mo, Dong-Liang
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03767