Fig. 2: Optimization of XB-catalyzed 2-deoxyglycosylation.
From: A robust and tunable halogen bond organocatalyzed 2-deoxyglycosylation involving quantum tunneling
[a] 2a (0.1 mmol), 1a–b (0.15 mmol), catalyst, 50 °C, solvent (0.2 M), time, argon. [b] Yield and α:β ratio were determined by crude 1H NMR spectra analysis using 1,3,5-trimethoxybenzene as an internal standard. [c] 40–50% NMR yields of Ferrier rearrangement side-products detected. [d] 92% 1b remaining. [e] 2a (0.2 mmol), 1b (0.30 mmol), catalyst, 50 °C, CH2Cl2 (0.2 M), time, argon. [f] Conducted at 40 °C. [g] Isolated yields. n.d. not determined, iPr isopropyl, TBAB tetrabutylammonium bromide, TBAI tetrabutylammonium iodide.
