This technology relates to a novel class of structurally rigid tricyclic chiral compounds based on hexahydropyrrolo[2,3-b]indole skeleton, which can be synthesized from a L-tryptophan derivative in five steps. The ligands can be used as an efficient chiral ligand in the enantioselective borane reduction of prochiral ketones to afford the corresponding alcohols in excellent yield and high enantioselectivities, or in the enatioselective carbon-carbon bond formation to novel tricyclic chiral compounds and their use in asymmetric catalysis, which is important in the field of pharmaceuticals.

File Number: NTU-TD/041/08