化学
光催化
质子化
对映选择合成
氢键
立体中心
离子键合
光化学
组合化学
有机化学
分子
催化作用
离子
作者
Zhen-Yao Dai,Zhong-Sheng Nong,Shun Song,Pu‐Sheng Wang
出处
期刊:Organic Letters
[American Chemical Society]
日期:2021-03-29
卷期号:23 (8): 3157-3161
被引量:37
标识
DOI:10.1021/acs.orglett.1c00801
摘要
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.
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