Asymmetric Addition of Alkoxy Ethynyl Anion to Chiral N-Sulfinyl Imines

The addition of lithiated ynol ethers to chiral N-sulfinyl imines proceeds in high yield and diastereoselectivity. The selectivity is completely reversed by the addition of boron trifluoride. These alkoxypropargyl sulfinamides can be reduced to afford enol ethers, selectively oxidized to busyl derivatives, or the ynol ether can be hydrolyzed to afford beta-amino esters.