α-Diazo-β-isoquinoline derivatives were obtained in excellent yields and enantioselectivities by asymmetric acyl-Mannich reaction of (diazomethyl)phosphonate or diazoacetate with isoquinolines.
A highly efficient TMSOTf-mediated asymmetric acetate-Mannich reaction of chiral isatin derived ketimines and S-phenyl thioacetate was developed to afford the direct synthesis of indole-based β3,3-amino acid thioester with excellent selectivity (dr > 98 : 2). Syntheses of (+)-AG-041R and 3-aminopyrroloindoline have been accomplished utilizing the method.
