title: Investigation of a dialkylation approach for enantioselective construction of vicinal quaternary stereocenters.
abstract: A detailed study of the dialkylation of dianions derived from dihydroisoindigo 1 with enantiopure ditriflate 2 is reported. The LHMDS-mediated process has been optimized to give C(2)-symmetric product 3 with high selectivity (C(2) selectivity 3:5 = 100:1; C(2):C(1) selectivity = 8:1). Stereoselection in the C(2) manifold is determined in both the bimolecular and intramolecular alkylation steps.
authors.affiliation: Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
authors.forename: S B
authors.initials: SB
authors.lastname: Hoyt
authors.forename: L E
authors.initials: LE
authors.lastname: Overman
mesh_terms: D000478:Alkylation; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D007211:Indoles; D011758:Pyrroles