Structure Guided Design of VANOL-Imidodiphosphorimidate Catalysts for the Catalytic Enantioselective Bromospiroketalization Reaction
Aliakbar Mohammadlou, Ankush Chakraborty, Mitchell Maday, Xiaopeng Yin, Zheng Li, Hadi Gholami, Kumar Dilip Ashtekar, Richard J. Staples, William D. Wulff, Babak Borhan
Abstract
This report presents a structure-guided approach for the optimization of VANOL-derived imidodiphosphorimidates as catalysts for the halonium-ion-induced spiroketalization reaction. Fine tuning of the catalyst active site, alongside enhanced acidity, was required to achieve high catalytic activity for the spiroketalization reaction. A wide range of substrates was well tolerated yielding halogenated spiroketals in high yields, diastereoselectivities, and enantioselectivities.
Topics & Concepts
CatalysisEnantioselective synthesisChemistryCombinatorial chemistryReaction conditionsOrganic chemistryVanadium and Halogenation ChemistryChemical Synthesis and ReactionsOxidative Organic Chemistry Reactions