Diastereoselective functionalization of Baylis-Hillman adducts: a convenient approach to alpha-methyl-alpha-amino acids

Abstract

The N-tosyl carbamates 4a-e, easily prepared starting from the Baylis-Hillman adducts 3a-e, underwent cyclization carried out with I(2)/NIS in the presence of NaH, to give the corresponding 2-oxo-1,3-oxazolidines 5a-e in good yield and total stereoselection when the substituent at C-5 is Ar. After the removal of tosyl group, followed by the cleavage of the heterocyclic ring, the alpha-methyl-alpha-amino acids 8a,b and 10 were obtained in good yield as hydrochlorides.