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

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

Michael J James  1 , James D Cuthbertson  1 , Peter O'Brien  1 , Richard J K Taylor  2 , William P Unsworth  3
Affiliations

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

Michael J James et al. Angew Chem Int Ed Engl. .

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.

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