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Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne.

ABSTRACT: A Rh-catalyzed 1,3-acyloxy migration of propargyl ester followed by intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne was developed. This tandem reaction provides access to bicyclic compounds containing a highly functionalized isotoluene or cyclohexenone structural motif, while only aromatic compounds were observed in related transition metal-catalyzed cycloadditions.

SUBMITTER: Huang S

PROVIDER: S-EPMC3334501 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne.

Huang Suyu S Li Xiaoxun X Lin Claire L CL Guzei Ilia A IA Tang Weiping W

Chemical communications (Cambridge, England) 20120117 16

A Rh-catalyzed 1,3-acyloxy migration of propargyl ester followed by intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne was developed. This tandem reaction provides access to bicyclic compounds containing a highly functionalized isotoluene or cyclohexenone structural motif, while only aromatic compounds were observed in related transition metal-catalyzed cycloadditions. ...[more]

PMID: 22252254

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