Journal of the American Chemical Society, Vol.129, No.20, 6398-6398, 2007
Two-step formal [3+2] cycloaddition of enones/enals and allenyl MOM ether: Gold-catalyzed highly diastereoselective synthesis of cyclopentanone enol ether containing an all-carbon quaternary center
A two-step, highly diastereoselective formal [3+2] cycloaddition between allenyl MOM ether and an enal/enone is developed. Au activation of allenyl ethers is proposed to yield all-carbon 1,3-dipoles, which can undergo concerted intramolecular 1,3-dipolar cycloadditions. Synthetically useful cyclopentanone enol ethers containing an all-carbon quaternary center can be readily prepared with excellent diastereocontrol.