α-Alkoxycarbonyl-α-hydroxy secondary amides from a carbamoylsilane and α-ketoesters

The addition of N-methoxymethyl-N-organylcarbamoyl(trimethyl)silane to alpha-ketoesters in anhydrous toluene at 60 degrees C afforded alpha-alkoxycarbonyl-alpha-siloxy amides in high yields (75-96%). The methoxymethyl was used as an amino protecting group and could be easily converted into hydrogen atom by simple acid hydrolysis leading to alpha-alkoxycarbonyl-alpha-hydroxy secondary amides. (c) 2017 Elsevier Ltd. All rights reserved.