title: Reactivity series for s-BuLi/diamine-mediated lithiation of N-Boc pyrrolidine: applications in catalysis and lithiation of N-Boc piperidine.
abstract: Using competition experiments between a range of ligands and (-)-sparteine, a reactivity series for N-Boc pyrrolidine lithiation using s-BuLi/diamines has been constructed; the results indicate that the s-BuLi/(+)-sparteine surrogate complex is more reactive than s-BuLi/(-)-sparteine and this has been exploited in the selection of ligand pairs for ligand exchange catalytic asymmetric lithiation of N-Boc pyrrolidine and lithiation of N-Boc piperidine.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, UK YO10 5DD.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: McGrath
authors.forename: Julia L
authors.initials: JL
authors.lastname: Bilke
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien