Anionic oxy-Claisen rearrangement of a tricyclic α-allyloxy ketone
JJ Kirchner, DV Pratt, PB Hopkins
Index: Kirchner, James J.; Pratt, Daniel V.; Hopkins, Paul B. Tetrahedron Letters, 1988 , vol. 29, # 34 p. 4229 - 4232
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Citation Number: 6
Abstract
Abstract Preparatively useful reaction conditions for the anionic oxy-Claisen rearrangement of an α-allyloxy ketone (6) possessing acidic α-and α′-hydrogens are described. The reaction rate and efficiency are strongly influenced by both solvent and counterion. The product, 8, although formally the product of [3, 3]-sigmatropic rearrangement of enolate 7, may in fact arise via a [2, 3]-Wittig followed by one or more [1, 2]-acyloin rearrangements.
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