Diels-Alder adducts of 2-acetoxyfuran as a route to 2, 3-functionalized 4-hydroxycyclohexanones. Application of X-ray diffraction to the problem of regio-and …

…, R Deziel, F Brisse, L Hechler

Index: Gravel, D.; Deziel, R.; Brisse, F.; Hechler, L. Canadian Journal of Chemistry, 1981 , vol. 59, p. 2997 - 3006

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Citation Number: 10

Abstract

The Diels-Alder adducts of 2-acetoxyfuran and maleic anhydride and 2-acetoxyfuran and chloromethylmaleic anhydride have been obtained and their dihydro derivatives manipulated in high yield to various 2, 3-functionalized 4-hydroxycyclohexanones. In all cases the hemiketal acetate bridge of the oxabicyclo [2.2. 1] derivatives was cleaved smoothly using sodium methoxide in methanol at 0° C; however, in the case of the ...