P(i-PrNCH₂CH₂)₃N: Efficient Catalyst for Synthesizing β-Hydroxyesters and α,β-Unsaturated Esters using α-Trimethylsilylethylacetate (TMSEA)

Kuldeep Wadhwa and John G. Verkade*

*Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011, Email: jverkadeiastate.edu

K. Wadhwa, J. G. Verkade, J. Org. Chem., 2009, 74, 4368-4371.

DOI: 10.1021/jo900477q

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Abstract

Activation of the silicon-carbon bond of α-trimethylsilylethylacetate in the presence of P(i-PrNCH₂CH₂)₃N as catalyst allows an efficient synthesis of β-hydroxyesters and α,β-unsaturated esters. Selectivity for either of these two products can be achieved simply by altering the catalyst loading and reaction temperature.

see article for more examples

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P(i-PrNCH₂CH₂)₃N as a Lewis Base Catalyst for the Synthesis of β-Hydroxynitriles Using TMSAN

K. Wadhwa, J. G. Verkade, J. Org. Chem., 2009, 74, 5683-5686.

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Key Words

β-hydroxy esters, α,β-unsaturated esters

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ID: J42-Y2009-1710