Methyl iodide mediated cleavage of the nitrogen-oxygen bond of isoxazolidines

DOI: 10.1016/S0040-4020(97)10125-9

Source and publish data:

Tetrahedron p. 16897 - 16910 (1997)

Update date:2022-07-29

Topics:

Authors:

Van Boggelen, Michel P.

Van Dommelen, Bart F. G. A.

Jiang, Shende

Singh, Gurdial

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Article abstract of DOI:10.1016/S0040-4020(97)10125-9

A novel method of N-O bond cleavage in isoxazolidines is described. Treatment of isoxazolidine with excess of methyl iodide in THF under reflux gave the quaternary ammonium iodide alcohol and the α,β-unsaturated aldehyde. The former can be converted to the latter via the Swern oxidation.

Full text of DOI:10.1016/S0040-4020(97)10125-9

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