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40.6 Product Class 6: 1-Oxa-2-azacycloalkanes

DOI: 10.1055/sos-SD-040-00778

Geffken, D.; Köllner, M. A.Science of Synthesis, (2009401083.

General Introduction

The synthesis of cyclic hydroxylamines has been reviewed up to 2005[‌1‌‌19‌] and can be found in HoubenWeyl, Vol. E 16a, p 4. Cycloaliphatic compounds containing a NO bond are valuable synthetic intermediates and have an essential role as pharmacophores/toxophores in bioactive compounds of natural and synthetic origin. Isoxazolidine and tetrahydro-2H-1,2-oxazine (1,2-oxazinane) synthesis has been developed intensively since the late 1980s, mostly focusing on stereoselective cycloaddition reactions. The synthesis of medium-sized 1-oxa-2-azacycloalkanes however, has remained difficult until now. More recently, ring-closing metathesis methodology has been successfully applied for the synthesis of a variety of heterocycles containing the 1,2-oxaza group. Solid-support preparation of cyclic hydroxylamines as an alternative process to solution-phase synthesis may become an important and attractive synthetic strategy, especially for the construction of compound libraries in drug and agricultural chemistry.

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