Synthesis of new chiral N-arylsulfonyl-1,3-oxazolidin-2-ones from α-amino acids

A variety of new chiral N-arylsulfonyl-1,3-oxazolidin-2-ones were prepared in three steps starting from (d)- and (l)-amino acid. N-Arylsulfonyl amino alcohols, derived from amino acids, were carbonylated with the bis-(trichloromethyl) carbonate (BTC), in the presence of triethylamine, to provide optically pure N-phenylsulfonyloxazolidin-2-ones 3a–f, N-naphthylsulfonyloxazolidin-2-ones 3g–j and N-tosylsulfonyloxazolidin-2-ones 3k–p in good yields.