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

Robert B. Lettan, II, Chris V. Galliford, Chase C. Woodward and Karl A. Scheidt*

*Department of Chemistry, Northwestern University, Evanston, Illinois 60208, Email: scheidtnorthwestern.edu

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

DOI: 10.1021/ja808811u (free Supporting Information)


Abstract

Addition of amide enolates to acylsilanes generates β-silyloxy homoenolates by undergoing a 1,2-Brook rearrangement. These unique nucleophiles formed in situ can then undergo addition to alkyl halides, aldehydes, ketones, and imines. γ-Amino-β-hydroxy amide products derived from a diastereoselective addition to N-diphenylphosphinyl imines can be efficiently converted to γ-lactams.

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

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


Key Words

Brook rearrangement, β-hydroxy amides, y-lactams, Microwave Synthesis


ID: J48-Y2009-1990