Article Palladium/Xu-Phos-Catalyzed Enantioselective Cascade Heck/Remote C( <i>sp<sup>2</sup></i>)−H Alkylation Reaction
Social Science Research Network(2021)
Abstract
Heck-type C-H bond activation of unactivated alkenes has emerged as a powerful strategy for the construction of synthetically valuable spirocycles over past 30 years, however, the development of asymmetric version has lagged largely behind. Herein we demonstrate a robust Heck-type reaction of a broad range of unactivated alkenes enabled by the first palladium/Xu-Phos-catalyzed tandem Heck/remote C−H bond alkylation. Moreover, both enantiomers of the product can be efficiently prepared using the same enantiomer of a chiral ligand via a position of the phenyl ring-dependent enantiodivergent synthesis. The salient features of this methodology include operational simplicity, high chemo- and enantioselectivity, broad substrate scope. In addition, we first revealed that the C(sp2)-H activation, alkene insertion and C−I reductive elimination steps are reversible by experiments.
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