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. 2008 Mar 26;130(12):3740-1.
doi: 10.1021/ja800001h. Epub 2008 Mar 1.

Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates

Guotao Li  1 , Guozhu Zhang, Liming Zhang
Affiliations

Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates

Guotao Li et al. J Am Chem Soc. .

Abstract

Propargylic pivalates with electronically unbiased internal alkynes are selectively transformed into (1Z,3E)-2-pivaloxy-1,3-dienes containing various functionalities. The unusual selectivity of 1,2-acyloxy migration over the structurally preferred 3,3-rearrangement is realized. This reaction is highly stereoselective and offers rapid access to dienes for one-pot intra-/intermolecular Diels-Alder reactions either under thermal conditions or with Lewis acid catalysis.

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