Asymmetric Synthesis of Isoquinoline Derivatives from Amino Acids.

Abstract

Fused pyridine derivatives R 0450Asymmetric Synthesis of Isoquinoline Derivatives from Amino Acids. -Reaction of isoquinolines (I) and (XIV) (cf. following scheme) with N-arylsulfonylamino acid fluorides (II) provides a straightforward and highly stereoselective access towards dihydroimidazoisoquinolines. A variety of reactions at the enamine moiety is studied. They involve the double bond hydrogenation, dimerization and highly stereoselective epoxidation reaction. Regiospecific and highly stereoselective oxirane ring opening of the epoxide (VIII) is achieved with diverse nucleophiles like amines, methanol or Tms-O-Tf (to be continued). -(SIECK, O.; EHWALD, M.; LIEBSCHER*, J.; Eur.