Synthesis ofenantioenriched cyclopropenes from alkynes and methyl arylvinyldiazoacetateswas achieved using Rh2(S-DOSP)4 as catalyst. 3-vinylcyclopropenes with quaternary stereogeniccenters can be readily accessed. Under more vigorous conditions, thesecyclopropenes undergo a regiospecific rearrangement to cyclopentadienes.  Density Functional calculations werecarried out to determine the exact transition state structure of thecyclopropenation reaction. The full scope and details of the study will bedescribed.

Highly enantioselective rhodium-catalyzed cyclopropenation
of terminal alkynes with styryldiazoacetates

240th National Meeting (2010)

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Highly enantioselective rhodium-catalyzed cyclopropenation of terminal alkynes with styryldiazoacetates