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

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, 5683-5686.

DOI: 10.1021/jo900814t (free Supporting Information)


Abstract

A low loading of a proazaphosphatrane compound efficiently catalyzes the reaction of trimethylsilylacetonitrile (TMSAN) with aldehydes for the synthesis of β-hydroxynitriles under mild reaction conditions. Various functional groups were tolerated, and good to excellent yields were obtained.


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

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


Key Words

nitriles, 1,2-addition, organocatalysis


ID: J42-Y2009-2410