Ester enolates from. alpha.-acetoxy esters. Synthesis of arylmalonic and. alpha.-arylalkanoic esters from aryl nucleophiles and. alpha.-keto esters

S Ghosh, SN Pardo, RG Salomon

Index: Ghosh, Subrata; Pardo, Simon N.; Salomon, Robert G. Journal of Organic Chemistry, 1982 , vol. 47, # 24 p. 4692 - 4702

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Citation Number: 32

Abstract

Ester enolates are generated by reductive a-deacetoxylation of a-acetoxy-a-arylmalonic esters or a-acetoxya-arylalkanoic esters with lithium in liquid ammonia or sodium a- (dimethy1amino) naphthalenide in hexamethylphosphoramide-benzene. Since the requisite a-acetoxy esters are available from aryl nucleophiles, the reductions provide effective new synthetic routes to arylmalonic esters and a-arylalkanoic esters. For example, 2-(p- ...

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