The Journal of organic chemistry

Grubbs Cross-Metathesis Pathway for a Scalable Synthesis of γ-Keto-α, β-unsaturated Esters

RN Nair, TD Bannister

Index: Nair, Reji N.; Bannister, Thomas D. Journal of Organic Chemistry, 2014 , vol. 79, # 3 p. 1467 - 1472

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Citation Number: 10

Abstract

A direct and scalable route to γ-keto-α, β-unsaturated esters, useful intermediates in medicinal chemistry and natural products synthesis, is reported. The key step involves the use of Grubbs' second-generation olefin metathesis catalyst for cross-metathesis of alkyl acrylates and 2° allylic alcohols. The metathesis step is followed by oxidation to give the desired products in high yield on scales of up to 25 g.