Tetrahedron Letters 2011-06-01

A Mild, Large-Scale Synthesis of 1,3-Cyclooctanedione: Expanding Access to Difluorinated Cyclooctyne for Copper-Free Click Chemistry.

EvanA Sims, ColeA Deforest, KristiS Anseth

Index: Tetrahedron Lett. 52(16) , 1871-1873, (2011)

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Abstract

We report the large-scale synthesis of 1,3-cyclooctanedione in five steps with 29% yield. This molecule is a synthetic precurser to difluorinated cyclooctyne, which participates in a bioorthogonal copper-free click reaction with azides. The final step demonstrates the first successful application of the Wacker-Tsuji oxidation to form a cyclic 1,3-dione.