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

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.

SUBMITTER: Mauleon P

PROVIDER: S-EPMC2711638 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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

Mauleón Pablo P Zeldin Rachel M RM González Ana Z AZ Toste F Dean FD

Journal of the American Chemical Society 20090501 18

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. ...[more]

PMID: 19378998

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