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Ester homologation via α-bromo α-keto dianion rearrangement

Conrad J. Kowalski, M. Serajul Haque and Kevin W. Fields

*Synthetic Chemistry Department, Smith Kline and French Laboratories, P.O. Box 7929, Philadelphia, Pennsylvania 19101

C. J. Kowalski, M. S. Haque, K. W. Fields, J. Am. Chem. Soc., 1985, 107, 1429-1430.

DOI: 10.1021/ja00291a063


Treatment of esters with dibromomethyllithium, followed by nBuLi and an acidic methanol quench, results in the formation of homologated esters.

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proposed reaction pathway

Key Words

Kowalski Ester Homologation

ID: J48-Y1985