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 applicability of the electron‐rich alkene 1 as synthon in organic synthesis. Copyright © 1986 Journal of Heterocyclic Chemistry
Reactions of ketenes. XX. Phenylketene dimethylacetal as synthon for the introduction of functionalized phenylethyl units / Graziano, M. L.; Iesce, M. R.; Scarpati, R.. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - 23:2(1986), pp. 553-556. [10.1002/jhet.5570230249]
Reactions of ketenes. XX. Phenylketene dimethylacetal as synthon for the introduction of functionalized phenylethyl units
Graziano M. L.;Iesce M. R.;
1986
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 applicability of the electron‐rich alkene 1 as synthon in organic synthesis. Copyright © 1986 Journal of Heterocyclic ChemistryI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
