Aldehydes, alcohols and enol acetates via reductive homologation of esters

CJ Kowalski, MS Haque

Index: Kowalski, Conrad J.; Haque, Serajul Journal of the American Chemical Society, 1986 , vol. 108, # 6 p. 1325 - 1327

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Citation Number: 28

Abstract

Quenching solutions of enolate anions 4 from these reductions with aqueous acid afforded aldehydes 6 directly, but the yields were very poor (eg, 22% for 9-11). Since these conditions seemed too vigorous for the sensitive aldehyde functionality, the reactions were first quenched with C1SiMe3 to generate silyl enol ethers 5. Although these silyl ethers could be isolated (eg, in 71% yield starting from ester 9), they could also be hydrolyzed in ...