Silver(I)- or copper(II)-mediated dearomatization of aromatic ynones: direct access to spirocyclic scaffolds

Michael J James; James D Cuthbertson; Peter O'Brien; Richard J K Taylor; William P Unsworth

doi:10.1002/anie.201501812

Silver(I)- or copper(II)-mediated dearomatization of aromatic ynones: direct access to spirocyclic scaffolds

Angew Chem Int Ed Engl. 2015 Jun 22;54(26):7640-3. doi: 10.1002/anie.201501812. Epub 2015 May 8.

Authors

Michael J James¹, James D Cuthbertson¹, Peter O'Brien¹, Richard J K Taylor², William P Unsworth³

Affiliations

¹ University of York, York (UK).
² University of York, York (UK). richard.taylor@york.ac.uk.
³ University of York, York (UK). william.unsworth@york.ac.uk.

PMID: 25960013
DOI: 10.1002/anie.201501812

Abstract

A high-yielding silver(I)- or copper(II)-catalyzed dearomatizing spirocyclization strategy allows the conversion of simple aromatic compounds that contain ynone substituents, including indole, anisole, pyrrole, and benzofuran derivatives, into functionalized spirocyclic scaffolds. A high-yielding asymmetric variant furnishes spirocyclic indolenines in up to 89:11 e.r.

Keywords: asymmetric catalysis; dearomatization; indolenines; silver; spirocycles.