Cyclopropene Derivatives as a New Entry to Enantioenriched Cyclopropanol and n-Butenal Pessessing Quaternary Carbon Stereocenters

Marwan Simaan, Chemistry, Technion, Haifa, Israel
Ilan Marek, Chemistry, Technion, Haifa, Israel

The Diastereoselective Carbocupration reaction of cycloropylmethyl ethers followed by addition of oxenoid leads to the formation of diastereo- and enantiomerically enriched 1,2,3- trisubstituted cyclopropanol species. A subsequent ring-fragmentation of the copper cyclopropanolate, leads to acyclic butenal derivatives possessing Alpha-quaternary carbon stereocenters in a single pot operation.