Abstract
AbstractA method for the preparation of 5‐aryl‐2,3‐dihydrofuran‐4‐carboxylates has been developed. Exposure of 4‐(arylmethyl)oxy‐2‐diazobutyrates to 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) effected oxidative generation of oxocarbenium intermediates, which underwent intramolecular attack of the diazo carbon atom and subsequent β‐elimination to give 5‐aryl‐2,3‐dihydrofurancarboxylates in modest to good yields. In particular, tertiary arylmethyl ethers offer the advantages of enhanced reactivity toward DDQ and higher product yields due to a Thorpe−Ingold effect. To demonstrate the synthetic utility of the cyclization reaction, selective transformations of an aromatization‐prone dihydrofuran product are also described.
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