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. 2009 May 13;131(18):6348-9.
doi: 10.1021/ja901649s.

Ligand-controlled access to [4 + 2] and [4 + 3] cycloadditions in gold-catalyzed reactions of allene-dienes

Pablo Mauleón  1 , Rachel M Zeldin, Ana Z González, F Dean Toste
Affiliations

Ligand-controlled access to [4 + 2] and [4 + 3] cycloadditions in gold-catalyzed reactions of allene-dienes

Pablo Mauleón et al. J Am Chem Soc. .

Abstract

By adjustment of the electronic properties of the ancilliary ligands, high selectivity can be achieved for either [4 + 2] or [4 + 3] cycloaddition reactions of allene-dienes catalyzed by gold(I). Triarylphosphitegold(I) complexes are employed as catalysts for a [4 + 2] cycloaddition reaction leading to alkylidenecyclohexenes. Conversely, di-tert-butylbiphenylphosphinegold(I)-catalyzed reactions afford cycloheptadienes via [4 + 3] cycloaddition reactions.

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Figures

Scheme 1
Scheme 1
[4+2]-Cycloaddition of Allene-dienes
Scheme 2
Scheme 2
[4+3]-Cycloaddition of Allene-dienes
See this image and copyright information in PMC

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