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Azetidines are increasingly important heterocycles found in a variety of natural products and pharmaceutical compounds. Protected 3-haloazetidines, widely used and versatile building blocks in medicinal chemistry, have been prepared in a one-pot, gram-scale strain-release reaction of 1-azabicyclo[1.1.0]butane from commercially available starting materials. These intermediates were subsequently used to prepare a series of high value azetidine-3-carboxylic acid derivatives including the first reported synthesis of 1-(tert-butoxycarbonyl)-3-((trifluoromethyl)thio)azetidine-3-carboxylic acid.

An improved, gram-scale synthesis of protected 3-haloazetidines: rapid diversified synthesis of azetidine-3-carboxylic acids