Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis
Marie Deliaval, Ramasamy Jayarajan, Lars Eriksson, Kálmán J. Szabó
Abstract
High Resolution Image Download MS PowerPoint Slide We have developed a new three-component catalytic coupling reaction of alkynyl boronates, diazomethanes, and aliphatic/aromatic ketones in the presence of BINOL derivatives. The reaction proceeds with a remarkably high enantio- and diastereoselectivity (up to three contiguous stereocenters) affording tertiary CF 3 -allenols in a single operational step. The reaction proceeds under mild, neutral, metal-free conditions, which leads to a high level of functional group tolerance.
Topics & Concepts
ChemistryStereocenterOrganocatalysisTrifluoromethylComponent (thermodynamics)CatalysisFunctional groupEnantioselective synthesisCombinatorial chemistryOrganic chemistryPolymerPhysicsThermodynamicsAlkylFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods