Rearrangements of ylides generated from reactions of diazo compounds with allyl acetals and thioketals by catalytic methods. Heteroatom acceleration of the [2, 3]- …

…, JH Griffin, MS Chinn, D Van Leusen

Index: Doyle, Michael P.; Griffin, John H.; Chinn, Mitchell S.; Leusen, Daan van Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 1917 - 1925

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Citation Number: 115

Abstract

Allyl acetals undergo ylide generation in rhodium (II) acetate catalyzed reactions with diazo esters with subsequent production of 2, 5-dialkoxy-4-alkenoates by the [2, 3]-sigmatropic rearrangement in moderate to good yields. The synthetic versatility of this class of polyfunctional compounds has been examined with selected transformations. Cyclopropanation and Stevens rearrangement compete with the [2, 3]-sigmatropic ...