Single-Flask Multicomponent Synthesis of Highly Substituted α-Pyrones Via a Sequential Enolate Arylation and Alkenylation Strategy

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2016 Nov 5

PMID 27768319

Citations 1

Authors

Michael Grigalunas

Olaf Wiest

Paul Helquist

Affiliations

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Abstract

Trisubstituted α-pyrones are obtained by a Pd-catalyzed three-component, single-flask operation via an α-arylation, subsequent α-alkenylation, alkene isomerization, and dienolate lactonization. A variety of coupling components under mild conditions afforded isolated yields of up to 93% of the pyrones with complete control of regioselectivity. Metal dependence was noted for three of the steps of the pathway. Utility of the pyrone products was demonstrated by further transformations providing convenient access to polyaromatic compounds, exhibiting broad molecular diversity.

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Jana S, Roy A, Lepore S Chem Commun (Camb). 2017; 53(37):5125-5127.

PMID: 28435948 PMC: 5510162. DOI: 10.1039/c7cc01708a.

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