title: Synthesis and resolution of a novel chiral diamine ligand and application to asymmetric lithiation-substitution
abstract: A short, efficient synthesis of chiral 1,5-diaza-cis-decalins (7) is presented. In the lithiation of N-Boc pyrrolidine, the ligands with the smallest most electron rich R groups (Me > Et > CH2tBu > CH2CF3 approximately Bn) were most effective. In the asymmetric deprotonation/substitution of benzylic substrates, (R,R)-7 (R = Me, R' = H) conferred modest selectivity. The ready availability of both enantiomers of the 1,5-diaza-cis-decalins and the ability to tune steric and electronic properties renders these compounds an attractive new class of diamine ligands.
authors.affiliation: Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia 19104, USA.
authors.initials: X
authors.lastname: Li
authors.initials: LB
authors.lastname: Schenkel
authors.initials: MC
authors.lastname: Kozlowski