Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles
Quentin D. Tercenio, Erik J. Alexanian
Abstract
The stereospecific cross-coupling of easily accessed electrophiles holds significant promise in the construction of C-C bonds. Herein, we report a nickel-catalyzed reductive coupling of allyl alcohols with chiral, nonracemic alkyl tosylates. This cross-coupling delivers valuable allylation products with high levels of stereospecificity across a range of substrates. The catalytic system consists of a simple nickel salt in conjunction with a commercially available reductant and importantly represents a rare example of a cross-coupling involving the C-O bonds of two electrophiles.
Topics & Concepts
ElectrophileStereospecificityChemistryCatalysisAlkylAlcoholNickelCombinatorial chemistryCoupling (piping)Medicinal chemistryOrganic chemistryMechanical engineeringEngineeringCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Synthesis and Catalysis