Isomerization of Allenyl Carbinol Esters

By: William Sommer, Aldrich ChemFiles 2009, 9.5, 8.

Aldrich ChemFiles 2009, 9.5, 8.

In 2007, Buzas et al. reported the synthesis of a series of 1,3-butadien- 2-ols from different allenes using a gold complex as catalyst.1 Butadiene building blocks are of interest for Diels-Alder reactions, [4+1] cycloaddition and asymmetric hydrogenation. However, only a few methods exist to access these interesting building blocks. In this report, the catalyst utilized in this reaction is a XPhos-gold complex. With mild reaction conditions and a low loading of 1 mol % of catalyst, the authors were able to synthesize a variety of butadienes with yields up to 100% (Scheme 4).

Scheme 4.

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  1. Buzas, A. K. et al. Org. Lett. 2007, 9, 985.

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