Iodocyclisation studies on unsaturated α-hydroxy esters

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 t...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 40; pp. 7415 - 7418
Main Authors Macritchie, Jacqueline A., Peakman, Torren M., Silcock, Alan, Willis, Christine L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.10.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STEREOSELECTIVE APPROACH
ALDOL-CYCLIZATION SEQUENCE
ACIDS
HOMOALLYLIC ALCOHOLS
CONSTRUCTION
CYCLIC ETHERS
SUBSTITUTED TETRAHYDROFURANS
STEREOCONTROLLED SYNTHESIS
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Summary: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. Iodocyclisation of ethyl 2-hydroxypent-4-enoate gave the syn and anti γ-lactones rather the expected substituted tetrahydrofuran. Oxygen-18 studies revealed that the mechanism of iodolactonisation varies depending on the reaction conditions employed.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01611-6