Chapter 5.7 Five-membered ring systems with O & N atoms

Add time:08/08/2019    Source:sciencedirect.com

Publisher SummaryThis chapter discusses the five-membered ring systems with O & N atoms such as Isoxazoles, Isoxazolines, Isoxazolidines, Oxazoles, Oxazolines, Oxazolidines, and Oxadiazoles. An efficient procedure for the synthesis of isoxazoles suitable for a multi-kilogram scale is shown in the chapter. “Fluorous synthesis”, a strategic alternative to conventional solid-phase synthesis, is illustrated by the preparation of a small isoxazoline library. The isoxazolines are detached from the fluorous label by treatment with pyridine hydrofluoride. The chiral titanium cornplex promotes the exo-selective and enantioselective 1, 3-dipolar cycloaddition of the unsaturated acylsuccinimide to the nitrones to yield the isoxazolidines. N-Acylisoxazolin-5-ones lose carbon dioxide on thermolysis or photolysis to give transient iminocarbenes, which undergo cyclisation to yield oxazoles.

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