Highly regioselective cleavages and iodinations of cyclic ethers utilizing SmI2.
Various functionalized cyclic ethers such as oxiranes, oxetanes, and tetrahydrofurans have been prepared, and the regiochemistry of their ring opening with samarium diiodide and acyl chloride or anhydride has been investigated. Alkyl-substituted oxetane 5 and tetrahydrofurans 1 and 2 show almost no regioselectivity. However, high regioselectivities from the branched cyclic ethers (3, 8, 9, and 10) containing ethereal or hydroxyl moieties have been observed. This is probably the result of the bidentate chelated species between samarium and oxygen.
Kwon
Doo Won
DW
Department of Chemistry, Center for Molecular Design and Synthesis, Korea Advanced Institute of Science and Technology, Daejon, Korea.
Kim
Yong Hae
YH
Lee
Kieseung
K