Diastereoselective Construction of α-Quaternary Carbon Centers in the Chiral-Auxiliary-Mediated Aza-Claisen Rearrangement of Ketene N-Allyl-N,O-acetals

Article abstract of DOI:10.1055/s-1988-27574

The aza-Claisen rearrangement of ketene N-allyl-N,O-acetals has been applied to the diastereoselective construction of precursors of 2-quaternary 4-pentenoic acids (82-97percent ds).Best yields are obtained when alkoxides are used to deprotonate the intermediate oxazolinium salts.