Nickel-Catalyzed Remote Asymmetric Hydroalkylation of Alkenyl Ethers to Access Ethers of Chiral Dialkyl Carbinols,Journal of the American Chemical Society

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Nickel-Catalyzed Remote Asymmetric Hydroalkylation of Alkenyl Ethers to Access Ethers of Chiral Dialkyl Carbinols
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-04-26 , DOI: 10.1021/jacs.3c02950
Jia-Wang Wang _{1,

2} , Zhen Li ₁ , Deguang Liu ₁ , Jun-Yang Zhang ₁ , Xi Lu ₃ , Yao Fu ₁

Affiliation

Site- and enantio-selective alkyl–alkyl bond formation is privileged in the retrosynthetic analysis due to the universality of sp³-hybridized carbon atoms in organic molecules. Herein, we report a nickel-catalyzed remote asymmetric hydroalkylation of alkenyl ethers via synchronous implementation of alkene isomerization and enantioselective C(sp³)–C(sp³) bond formation. Regression analysis of catalyst structure–activity relationships accelerates the rational ligand modification through modular regulation. This reaction has several advantages for synthesizing chiral dialkyl carbinols and their ether derivatives, including the broad substrate scope, good functional group tolerance, excellent regioselectivity (>20:1 regioisomeric ratio), and high enantioselectivity (up to 95% enantiomeric excess).

中文翻译：

镍催化的烯基醚远程不对称加氢烷基化获得手性二烷基甲醇的醚

由于 sp ³杂化碳原子在有机分子中的普遍性，位点和对映选择性烷基-烷基键的形成在逆合成分析中具有优势。在此，我们报道了通过烯烃异构化和对映选择性 C(sp ³ )–C(sp ^{3的同步实施，镍催化的烯基醚的远程不对称加氢烷基化}）债券形成。催化剂结构-活性关系的回归分析通过模块化调节加速了合理的配体修饰。该反应在合成手性二烷基甲醇及其醚衍生物方面具有多种优势，包括底物范围广、官能团耐受性好、区域选择性好（>20:1 区域异构比）和高对映选择性（对映体过量高达 95%）。

更新日期：2023-04-26

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