Efficient synthesis of 2-hydroxycyclobutanone derivatives; application to the synthesis of 1,4-diketones and cyclopentenones

Abstract

Treatment of 4,4-(trimethylenedithio)butanal meso-1,2-diphenylethylene acetal (3) with butyl-lithium gave a high yield of 2,2-(trimethylenedithio)cyclobutanol (8), which was transformed into 2-tetrahydropyran-2-yl-oxycyclobutanone (11), a potential intermediate for the synthesis of 1,4-diketones and cyclopentenones.