Asymmetric Synthesis of α-Amino Acids via Cationic Aza-Cope Rearrengements

Article abstract of DOI:10.1016/S0040-4020(01)87201-X

Ene-iminium intermediates resulting from reaction between glyoxal and β-amino alcohols rearrange by an aza-Cope process.Three different tandem reactions are thus carried out; their first component is this cationic rearrangement, the second step being either an iminium hydrolysis, a nucleophile-induced ene-iminium cyclization or a Mannich reaction.The last two sequences lead to homochiral proline derivatives.