Asymmetric Photocatalytic C(sp3)–H Bond Addition to α-Substituted Acrylates
| Autor: | Zhen-Yao Dai, Pu-Sheng Wang, Zhong-Sheng Nong, Shun Song |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Hydrogen bond Chemistry Organic Chemistry Enantioselective synthesis Ionic bonding Protonation Hydrogen atom 010402 general chemistry Hydrogen atom abstraction 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Photocatalysis Physical and Theoretical Chemistry Phosphoric acid |
| Zdroj: | Organic Letters. 23:3157-3161 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.1c00801 |
| Popis: | Asymmetric functionalization of inert C(sp3)-H bonds is a straightforward approach to realize versatile bond-forming events, allowing the precise assembly of molecular complexity with minimal functional manipulations. Here, we describe an asymmetric photocatalytic C(sp3)-H bond addition to α-substituted acrylates by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst and chiral phosphoric acid as a chiral proton-transfer shuttle. This protocol is supposed to occur via a radical/ionic relay process, including a TBADT-mediated HAT to cleave the inert C(sp3)-H bond, a 1,4-radical addition, a back hydrogen abstraction, and an enantioselective protonation. A variety of inert C-H bond patterns and α-substituted acrylates are well tolerated to enable the rapid synthesis of enantioenriched α-stereogenic esters from simple raw materials. |
| Databáze: | OpenAIRE |
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