The Reaction of Nitrones with Cyclopropanes: A Convenient Preparation of Tetrahydro-1,2-oxazines

Abstract

Nitrones and dialkyl cyclopropane-1,1-dicarboxylates undergo smooth reaction in the presence of ytterbium(III) triflate to form tetrahydro-1,2-oxazines with a high degree of regio- and stereocontrol. A three-component protocol has also been developed wherein the nitrone is generated in situ from an aldehyde and a hydroxylamine. The reactions are often high yielding with broad substrate scope. The multicomponent nature of the reaction makes it amenable to the synthesis of compound libraries and also allows for highly convergent strategies to be developed in target-oriented synthesis.

Key words

cycloadditions - nitrones - tetrahydro-1,2-oxazines - cyclopropanes - hydroxylamines

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