Synthetic applications (II) of the tandem [2,3]-Wittig-anionic oxy-Cope rearrangement: Stereoselective trisubstituted δ-lactone and tetrahydropyran synthesis

DOI: 10.1016/S0040-4039(97)01475-5

Source and publish data:

Tetrahedron Letters p. 6453 - 6456 (1997)

Update date:2022-08-03

Topics:

Authors:

Greeves, Nicholas

Lee, Wai-Man

Barkley, Jim V.

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Article abstract of DOI:10.1016/S0040-4039(97)01475-5

Di- and trisubstituted δ-lactones have been prepared by stereoselective iodolactonisation and phenylselenolactonisation of δ,ε-unsaturated carboxylic acids. The acyclic stereochemistry of the acids arises from highly stereoselective tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of cinnamyl ethers with potassium hydride and 18-crown-6 in THF to give δ,ε-unsaturated aldehydes.

Full text of DOI:10.1016/S0040-4039(97)01475-5

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