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Synthesis of Tertiary β-Hydroxy Amides by Enolate Additions to Acylsilanes

Robert B. Lettan II, Troy E. Reynolds, Chris V. Galliford and Karl A. Scheidt*

*Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, Email:

R. B. Lettan II, T. E. Reynolds, C. V. Galliford, K. A. Scheidt, J. Am. Chem. Soc., 2006, 128, 15566-15567.

DOI: 10.1021/ja065605v

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The addition of amide enolates to acylsilanes and a subsequent 1,2-Brook rearrangement generate β-silyloxy homoenolates nucleophiles that undergo smooth addition to alkyl halides, aldehydes, and ketones.

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reaction pathway

Amide Enolate Additions to Acylsilanes: In Situ Generation of Unusual and Stereoselective Homoenolate Equivalents

R. B. Lettan, II, C. V. Galliford, C. C. Woodward, K. A. Scheidt, J. Am. Chem. Soc., 2009, 131, 8805-8814.

Key Words

1,2-Brook Rearrangement, β-Hydroxy amides, Acylsilanes

ID: J48-Y2006-3970