Reactions of ketenes. XX. Phenylketene dimethylacetal as synthon for the introduction of functionalized phenylethyl units

ML Graziano, MR Iesce…

Index: Graziano, Liliana M.; Iesce, Rosaria M.; Scarpati, Rachele Journal of Heterocyclic Chemistry, 1986 , vol. 23, p. 553 - 556

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Citation Number: 5

Abstract

Abstract Phenylketene dimethylacetal (1) reacts with the α-diazoketones to give the dihydrofurans 6. These compounds, as cyclic ortho esters, can undergo dealcoholation into the furans 2 and hydrolysis into the γ-ketoesters 3 and into the γ-ketoacids 4. Cyclopropane acetal 8, obtained starting from acetal 1 and ethyl diazoacetate, by heating leads quantitatively to functionalized ester 9. These synthetic methods enlarge the sphere of ...