Article Palladium/Xu-Phos-Catalyzed Enantioselective Cascade Heck/Remote C( sp2)−H Alkylation Reaction
| Autor: | Danting Ji, Lujia Zhou, Junliang Zhang, Bing Xu, Yu Liu, Zhan-Ming Zhang, Lizuo Wu |
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| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
History Polymers and Plastics Alkene Chiral ligand Enantioselective synthesis chemistry.chemical_element Alkylation Combinatorial chemistry Industrial and Manufacturing Engineering Reductive elimination Catalysis chemistry Business and International Management Enantiomer Palladium |
| Zdroj: | SSRN Electronic Journal. |
| ISSN: | 1556-5068 |
| DOI: | 10.2139/ssrn.3936039 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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