Aldol Type Condensations of β-Keto Ester Dianions

Authors:
  • SHStuart Nicholas Huckin
    Stuart Nicholas Huckin
  • LWLarry Weiler
    Larry Weiler
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Abstract
The dianion of methyl acetoacetate reacts with ketones and aldehydes to yield δ -hydroxy-β-keto esters. These hydroxy esters can be dehydrated to the corresponding γ,δ-unsaturated-β-keto esters which are useful in annelation reactions to form cyclic β-keto esters. The dianion of methyl acetoacetate does not appear to undergo conjugate addition to simple α,β-unsaturated ketones, instead only carbonyl addition occurs.