Chiral Induction in Cycloaddition Reactions of Azomethine Ylides Derived from Secondary α-Amino Acids by the Decarboxylative Route

Article abstract of DOI:10.1016/S0040-4039(00)92401-8

Cyclic secondary α-amino acids react with isatin and menthyl acrylate via decarboxylative azomethine ylide formation and subsequent cycloaddition involving an endo-transition state to give cycloadducts in 67-82percent d.e.The stereochemistry of the major cycloadduct is assigned from a single crystal X-ray structure and a transition state model is proposed for the process. Key Words: 1,3-Dipole; cycloaddition; decarboxylation; chiral induction.