J. Macritchie, T. Peakman, A. Silcock
Oct 1, 1998
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Iodocyclisation of ethyl 2-hydroxyhex-5-enoate 1 and the homologous hept-6-enoate 4 under thermodynamic or kinetic conditions gave the novel tetrahydrofurans 2/3 and tetrahydropyrans 5/6 respectively. In contrast, ethyl 2-hydroxypent-4-enoate 7 gave iodolactones 9 and 10 in good yield, rather than the expected cyclic ether 8 . Oxygen-18 studies revealed that the mechanism of iodolactonisation of 7 is dependent upon the reaction conditions employed.