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

2010 ARKIVOC  
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 α-nitroarylated 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.
doi:10.3998/ark.5550190.0012.608 fatcat:onm7jv45z5gcndcf3enom6767u