Enantioselective synthesis of tetrahydroisoquinolines and benzazepines by silane terminated Heck reactions with the chiral ligands (+)-TMBTP and (R)-BITIANP

Abstract

The intramolecular Heck reaction of the iodoaryl compound 1 with a (Z)-allyl silane moiety in the presence of the chiral ligand (+)-TMBTP 13 leads to the benzazepine 5b with 92% ee, whereas 3 with an (E)-allyl silane moiety in the presence of the chiral ligand (R)-BITIANP 14 gives 5a with 91% ee; in a similar way, 9 and 10 were transformed in the presence of 13 into the tetrahydroisoquinolines 11b and 12b with 86 and 84% ee, respectively.