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