Home
Resources
Publications
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

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

Ning Zou, Ji-Wen Jiao, Yu Feng, Cheng-Xue Pan, Cui Liang, Gui-Fa Su, Dong-Liang Mo

Org Lett. 2019 Jan 18;21(2):481-485.

PMID: 30628783

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3094879	Iron(II) acetate		3094-87-9	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: