Investigations on transition-state geometry in the aldol condensation.

SE Denmark, BR Henke

Index: Denmark, Scott E.; Henke, Brad R. Journal of the American Chemical Society, 1991 , vol. 113, # 6 p. 2177 - 2194

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Citation Number: 92

Abstract

Abstract: Model compounds 1 and 2 have been studied to elucidate the relative orientation of enolate and carbonyl moieties in the aldol reaction. The syntheses of these compounds have been achieved from a common precursor derived from fragmentation of adamantane. Models of the limiting transition structures reveal that the cyclization must proceed through either a synclinal or antiperiplanar orientation of the aldehyde with respect to the enolate. ...

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