First Reported Catalytic Diastereo- and Enantioselective Hydroformylation of Cyclopropenes to make Chiral Formylcyclopropanes

An exciting new process to produce potentially useful formyl cyclopropanes from cyclopropenes has been invented by Professor Michael Rubin and PhD student Matt Sherrill. The products have great potential as pharmaceutical synthons, particularly in view of the controllable chirality induced by the rhodium-ligand catalyst. A multi-unit catalyst screening reactor was used to determine catalyst/ligand combinations that offer good yields and with regioselectivity and enantioselectivity. Work continues to further improve the enantioselectivity and to understand the observed electronic effects of the ligands.

This work was highlighted in Chemical and Engineering News, Oct. 6, 2008. (For more, please see Sherrill, W. M.; Rubin, M. "Rhodim-Catalyzed Hydroformylation of Cyclopropenes" J. Am. Chem. Soc. 2008 130(41) 13804-13809. DOI: 10.1021/ja805059f)