Nickel(0)-catalyzed cyclization of N-benzoylaminals for isoindolinone synthesis

Danielle M Shacklady-McAtee; Srimoyee Dasgupta; Mary P Watson

doi:10.1021/ol201248c

Nickel(0)-catalyzed cyclization of N-benzoylaminals for isoindolinone synthesis

Org Lett. 2011 Jul 1;13(13):3490-3. doi: 10.1021/ol201248c. Epub 2011 Jun 6.

Authors

Danielle M Shacklady-McAtee¹, Srimoyee Dasgupta, Mary P Watson

Affiliation

¹ Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.

PMID: 21644568
DOI: 10.1021/ol201248c

Abstract

A nickel(0) catalyst effectively mediates the cyclization of N-benzoyl aminals in the presence of a stoichiometric Lewis acid. This method enables preparation of a variety of isoindolinones with substitution on the benzoyl fragment and C-3 carbon. This reaction likely proceeds via an α-amidoalkylnickel(II) intermediate, which then may cyclize via either an electrophilic aromatic substitution or an insertion pathway.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzylamines / chemistry*
Catalysis
Cyclization
Isoindoles / chemical synthesis*
Molecular Structure
Nickel / chemistry*

Substances

Benzylamines
Isoindoles
Nickel
benzylamine