102127-47-9Relevant academic research and scientific papers
Simple large-scale preparation of 3,3-disubstituted cyclopropenes: Easy access to stereodefined cyclopropylmetals via transition metal-catalyzed hydrometalation
Rubin, Michael,Gevorgyan, Vladimir
, p. 796 - 800 (2004)
3,3-Disubstituted cyclopropenes have been readily prepared in a multigram scale via two different methods: (1) dehydrohalogenation of bromocyclopropanes, and (2) Rh-catalyzed addition of carbenoids to trimethylsilylacetylene followed by desilylation. Highly diastereoselective Pd-catalyzed hydrostannation and highly enantioselective Rh-catalyzed hydroboration of 3,3-disubstituted cyclopropenes afforded useful cyclopropylmetal building blocks in high yields.
Catalytic enantioselective hydroboration of cyclopropenes
Rubina, Marina,Rubin, Michael,Gevorgyan, Vladimir
, p. 7198 - 7199 (2007/10/03)
2,2-Disubstituted cyclopropyl boronates have been synthesized with high degrees of diastereo- and enantioselectivity via the rhodium-catalyzed asymmetric hydroboration of 3,3-disubstituted cyclopropenes. A strong directing effect of ester and alkoxymethyl substituents has been demonstrated. The directing effect was found to be necessary in achieving high degrees of enantiomeric induction. Selected cyclopropylboronic derivatives were successfully employed in the Suzuki cross-coupling reaction to produce the corresponding optically active aryl- and vinylcyclopropanes in good yields. Copyright
