Stereoselective Synthesis of 2,5-Dihydrofurans by Sequential SN2' Cleavage of Alkynyloxiranes and Ag(1+)-Catalyzed Cyclization of the Allenylcarbinol Products

Article abstract of DOI:10.1021/jo00077a048

The alkynyloxiranes 5a,b, 7, and 18 afford mainly the anti S_N2' products 6a,b, 8, and 19a upon treatment with Me2CuLi.The derived primary alcohol silyl ethers 9a,b, 10, and 19b-d undergo Ag(1+)-catalyzed cyclization to the 2,5-dihydrofurans 11a