P(i-PrNCH2CH2)3N: efficient catalyst for synthesizing beta-hydroxyesters and alpha,beta-unsaturated esters using alpha-trimethylsilylethylacetate (TMSEA).
We present an efficient synthesis of beta-hydroxyesters and alpha,beta-unsaturated esters via activation of the silicon-carbon bond of alpha-trimethylsilylethylacetate using catalytic amounts of the commercially available P(i-PrNCH(2)CH(2))(3)N 1a. Selectivity for either of these two products can be achieved simply by altering the catalyst loading and reaction temperature to afford addition or stereoselective condensation. This method is mild and tolerates a wide array of functional groups.
Wadhwa
Kuldeep
K
Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011, USA.
Verkade
John G
JG
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D017553:Phosphorus Compounds / Q000737:chemistry; D012821:Silanes / Q000737:chemistry
D000588:Amines; D004952:Esters; D017553:Phosphorus Compounds; D012821:Silanes