Brønsted Acid-Catalyzed Aza-Ferrier Reaction of N,O-Allenyl Acetals: Synthesis of ß-Amino-α-methylene Aldehydes.

ABSTRACT

A Tf2NH-catalyzed aza-Ferrier reaction of N,O-allenyl acetals was reported. This protocol provided various types of ß-amino-α-methylene aldehydes as the products. The N,O-allenyl acetal substrates were easily prepared by base-induced isomerization of N,O-propargyl acetals with Triton B. The N,O-propargyl acetals were prepared from the corresponding aldehydes or lactams. Further synthetic applications of the products were also described.