Enantioconvergent and Regioselective Synthesis of Allenylsilanes by Nickel-Catalyzed C(sp<sup>2</sup>)–C(sp<sup>3</sup>) Cross-Coupling Starting from Racemic α-Silylated Propargylic Bromides
Yan Xu, Hong Yi, Martin Oestreich
Abstract
A direct synthesis of enantioenriched allenylsilanes from racemic α-silylated propargylic bromides by an enantioconvergent nickel-catalyzed cross-coupling is reported. The high regioselectivity is governed by the bulky silyl group, and the C(sp2)–C(sp3) bond formation occurs exclusively at the γ-position of the propargyl electrophile. The level of enantioselection induced by a chiral Pybox ligand is moderate.
Topics & Concepts
ChemistryRegioselectivityElectrophilePropargylCatalysisNickelSilylationMedicinal chemistryLigand (biochemistry)StereochemistryOrganic chemistryReceptorBiochemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions