Boat/chair topographic stereoselection during anionic oxy-Cope rearrangement of 1-alkenyl-2-cyclopentenyl-endo-norbornan-2-ols

…, GD Maynard, RD Rogers, JC Gallucci…

Index: Paquette, Leo A.; Teleha, Christopher A.; Taylor, Richard T.; Maynard, George D.; Rogers, Robin D.; Gallucci, Judith C.; Springer, James P. Journal of the American Chemical Society, 1990 , vol. 112, # 1 p. 265 - 277

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Citation Number: 33

Abstract

Abstract: In order to examine which of four possible [3.3] sigmatropic transition states I- alkenyl-2-cyclopentenyl-endo-norbornan-2-01s would adopt during oxy-Cope rearrangement of their potassium salts at room temperature, the functionalized norbornanones 15, 19, 20, and 24-26 were prepared. Since those in the 3.3-dimethyl series are derived from (1R)-(-)-fewhone, they were available in optically pure form. ...