Investigation of a dialkylation approach for enantioselective construction of vicinal quaternary stereocenters.
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.
Hoyt
S B
SB
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
Overman
L E
LE
D000478:Alkylation; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D007202:Indicators and Reagents; D007211:Indoles; D011758:Pyrroles