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Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions.

ABSTRACT: Vinylcarbenes are versatile synthetic intermediates, capable of asymmetric cyclopropanation and insertion into unactivated C-H bonds. The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyldiazoacetates and, for the first time, allows the use of Z-vinylcarbenes in asymmetric C-H insertion and cyclopropanation reactions. Dirhodium azetidinone ligated compounds are optimal catalysts. Cyclopropanation coupled with the Cope rearrangement provides access to trans-3,4-disubstituted hydroazulenes.

SUBMITTER: Bykowski D

PROVIDER: S-EPMC2526162 | biostudies-literature | 2006 Dec

REPOSITORIES: biostudies-literature

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Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions.

Bykowski Darren D Wu Kou-Hui KH Doyle Michael P MP

Journal of the American Chemical Society 20061201 50

Vinylcarbenes are versatile synthetic intermediates, capable of asymmetric cyclopropanation and insertion into unactivated C-H bonds. The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyldiazoacetates and, for the first time, allows the use of Z-vinylcarbenes in asymmetric C-H insertion and cyclopropanation reactions. Dirhodium azetidinone ligated compounds are optimal catalysts. Cyclopropanation coupled with the Cope rearr ...[more]

PMID: 17165748

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