New catalytic systems based on a bis(1,3-disubstituted imidazoline 2-thione)-copper complex have been developed for the highly regioselective boration of internal alkynes.

An efficient method for the preparation of enantiomerically enriched 1,1-diarylalkyl units has been developed. The use of copper hydride complexed by the (R)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine (Josiphos) ligand effects a highly enantioselective conjugate reduction of beta,beta-diaryl-substituted alpha,beta-unsaturated nitriles with aryl groups of similar steric demand and no secondary coordination site. A range of substrates with meta and para substituents on the aryl group were reduced with good to excellent enantioselectivities (up to 97 % enantiomeric excess (ee)) and this methodology was applied to the formal synthesis of indatraline.

An efficient and highly enantioselective method for the preparation of (R)-tolterodine is described. The synthesis was performed by CuH-catalyzed asymmetric conjugate reduction of a beta,beta-diaryl-substituted unsaturated nitrile as a key step, which is prepared by a stereoselective hydroarylation of alkynenitrile with aryl boronic acid. The synthesis was accomplished without employing the protection-deprotection sequence.

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