Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines
Mingkai Zhang, Peilin Xu, Alex J. Vendola, Christophe Allais, Anne‐Marie Dechert Schmitt, Robert A. Singer, James P. Morken
Abstract
In this paper is described an easily synthesized chiral diazaborolidine that is inexpensive, stable, and provides excellent stereoselection across a number of reaction classes. These versatile compounds possess utility in four different classes of cycloaddition reactions, offering good yield and stereoselectivity. X-ray structure analysis provides insight about the origin of stereocontrol.
Topics & Concepts
Pericyclic reactionCycloadditionStereoselectivityYield (engineering)ChemistryComputational chemistryCombinatorial chemistryOrganic chemistryMaterials scienceCatalysisMetallurgyCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistryAsymmetric Hydrogenation and Catalysis