Stereoselective reactions of N-acyl-N,O-acetals with 2-(trimethylsilyloxy)furan

Article abstract of DOI:10.1016/S0040-4039(00)79378-6

Reactions of acyclic chiral N-acyl-N,O-acetals with 2-(trimethylsilyloxy)furan and BF₃ · Et₂O products 4-(aminoalkyl)-2-buten-4-olides in 30% to 62% yield and variable diastereomeric excesses of the syn (threo) stereoisomer. Selectivity is dependent on the structure of N-acyl-N,O-acetal used.