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. 2005 Apr 27;127(16):5802-3.
doi: 10.1021/ja051689g.

Synthesis of 2-cyclopentenones by gold(I)-catalyzed Rautenstrauch rearrangement

Xiaodong Shi  1 , David J Gorin, F Dean Toste
Affiliations

Synthesis of 2-cyclopentenones by gold(I)-catalyzed Rautenstrauch rearrangement

Xiaodong Shi et al. J Am Chem Soc. .

Abstract

The rearrangement of 1-ethynyl-2-propenyl pivaloates to cyclopentenones catalyzed by cationic triphenylphosphinegold(I) complexes is described. The reaction tolerates both alkyl and aryl substitution at the acetylenic and olefinic positions. Importantly, the gold(I)-catalyzed rearrangement of enantioenriched propargyl pivaloates proceeds with excellent chirality transfer, thus providing a practical method for the enantioselective synthesis of cyclopentenones.

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