Highly stereoselective and completely regiospecific method for the dehydration of. beta.-hydroxy esters via. beta.-alanoxy enolates. Application to the synthesis of …

JA Katzenellenbogen, T Utawanit

Index: Katzenellenbogen,J.A.; Utawanit,T. Journal of the American Chemical Society, 1974 , vol. 96, p. 6153 - 6158

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Citation Number: 40

Abstract

Abstract: The treatment of a/3-hydroxy ester with aluminum ethoxide or diethoxyaluminum chloride, followed by warming with added lithium diisopropylamide, produces the corresponding cu, P-unsaturated ester in moderate yield (44-56%). This process is completely regiospecific (no P, r isomers formed) and in suitably substituted cases is completely stereospecific, producing only the E olefin isomer. It is conceived that the ...