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Review | Regular issue | Vol 87, No. 9, 2013, pp.1835-1864
Published online, 16th July, 2013
DOI: 10.3987/REV-13-776
Synthesis of Functionalized Cyclic Molecules by Palladium-Catalyzed Cyclization of Propargylic Esters with Bis-nucleophiles

Masahiro Yoshida*

*Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan

Abstract

It is known that propargylic esters react with palladium complex leading to π-propargylpalladium complexes, which further cause various transformations in the presence of soft nucleophiles to produce the corresponding products. Among them, palladium-catalyzed cyclization of propargylic esters with bis-nucleophiles is one of the useful methodologies for the construction of functionalized cyclic molecules in one step. Since the pioneering work reported by Tsuji in 1985, a considerable number of reactions have been reported by the use of various bis-nucleophiles. In this review, a comprehensive overview of the studies on palladium-catalyzed reactions of propargylic esters with bis-nucleophiles is described, in which various functionalized cyclic molecules can be synthesized in a regio- and stereoselective manner.