tolterodine-tartrate and allyl-bromide

A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).

Topics: Allyl Compounds; Catalysis; Copper; Indicators and Reagents; Lithium; Methane; Molecular Structure; Organometallic Compounds; Stereoisomerism; Tolterodine Tartrate