Enantioselective Pd-Catalysed Deallylative Gamma-Lactonisation Of Propargyl Carbazolone Allyl Carbonates: Mechanistic Insight Into Their Decarboxylative Allylation
AUSTRALIAN JOURNAL OF CHEMISTRY（2014）
Abstract
Subjection of N-methyl carbazolone allyl carbonates bearing a propargyl side chain to Pd-0 catalysis leads to the formation of enantioenriched -lactones, rather than the expected products of decarboxylative allylation. This side reaction has not been observed with the enantioselective decarboxylative allylation of related -ketoesters, and provides evidence for a mechanism involving turnover limiting decarboxylation from the palladium carboxylate resting state. Following lactonisation, the Pd-0 catalyst is regenerated by Pd-II reductive alkyne coupling.
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