New multidendate phosphine ligands and their application in palladium-catalyzed asymmetric allylic alkylation

ORGN 655

Yuxin Pei, cathypei@kth.se, Emilie Brulé, emiliebrule@hotmail.com, and Christina Moberg, kimo@kth.se. Department of Chemistry/Organic Chemistry, Royal Institute of Technology, Teknikringen 30, S-100 44, Stockholm, Sweden
Asymmetric catalysis has been of great interest to chemists during the past decades, and efforts have been devoted to the synthesis of chiral ligands which introduce high enantioselectivity to product. Chiral ligands with rotational symmetry are often successful in asymmetric catalysis, due to the advantage of reducing the number of the possible transition states.

Due to our interest in ligands with C3 symmetry we needed easy access to chiral parent TREN compounds (1a), and found a convenient route using ring opening of chiral aziridines by ammonia. Analogues with C2 (1b) and C3 symmetry (1c) can be prepared in a similar way. By functionalization of the end amino groups new phosphine ligands were obtained via reaction with 2-(diphenylphosphino)benzoic acid. Their catalytic activity in asymmetric allylic alkylation is presently studied.