Enantioselective Pd-Catalysed Deallylative γ-Lactonisation of Propargyl Carbazolone Allyl Carbonates: Mechanistic Insight into their Decarboxylative Allylation
Quillon Simpson A , Robert Konrath A and David W. Lupton A B
+ Author Affiliations
- Author Affiliations
A School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.
B Corresponding author. Email: david.lupton@monash.edu
Australian Journal of Chemistry 67(9) 1353-1356 https://doi.org/10.1071/CH14211
Submitted: 3 April 2014 Accepted: 9 April 2014 Published: 13 May 2014
Abstract
Subjection of N-methyl carbazolone allyl carbonates bearing a propargyl side chain to Pd0 catalysis leads to the formation of enantioenriched γ-lactones, rather than the expected products of decarboxylative allylation. This side reaction has not been observed with the enantioselective decarboxylative allylation of related β-ketoesters, and provides evidence for a mechanism involving turnover limiting decarboxylation from the palladium carboxylate resting state. Following lactonisation, the Pd0 catalyst is regenerated by PdII reductive alkyne coupling.
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