Synthesis of nitroaryl derivatives of glycine via oxidative nucleophilic substitution of hydrogen in nitroarenes

Abstract

Carbanion of ethyl N- (1,3-dithiolan-2-ylidene)glycinate adds to activated nitroarenes mostly in para position to the nitro group. Subsequent oxidation of the resulting σ H adducts with DDQ gave respective αnitroarylated glycine derivatives in moderate yields. The reaction of esters of chiral alcohols such as (-)-menthol or (-)-8-phenylmenthol proceeds with a moderate or high diastereoselectivity leading to enantiomerically enriched nitroarylglycines.