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Asymmetric hydrogenation of ketimines with minimally different alkyl groups.
Wang, Mingyang; Liu, Shihan; Liu, Hao; Wang, Yujie; Lan, Yu; Liu, Qiang.
Afiliación
  • Wang M; Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, China.
  • Liu S; College of Chemistry and Molecular Sciences, Henan University, Kaifeng, China.
  • Liu H; Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, China.
  • Wang Y; Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, China.
  • Lan Y; School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing, China. lanyu@cqu.edu.cn.
  • Liu Q; College of Chemistry, Pingyuan Laboratory, Zhengzhou University, Zhengzhou, Henan, China. lanyu@cqu.edu.cn.
Nature ; 631(8021): 556-562, 2024 Jul.
Article en En | MEDLINE | ID: mdl-38806060
ABSTRACT
Asymmetric catalysis enables the synthesis of optically active compounds, often requiring the differentiation between two substituents on prochiral substrates1. Despite decades of development of mainly noble metal catalysts, achieving differentiation between substituents with similar steric and electronic properties remains a notable challenge2,3. Here we introduce a class of Earth-abundant manganese catalysts for the asymmetric hydrogenation of dialkyl ketimines to give a range of chiral amine products. These catalysts distinguish between pairs of minimally differentiated alkyl groups bound to the ketimine, such as methyl and ethyl, and even subtler distinctions, such as ethyl and n-propyl. The degree of enantioselectivity can be adjusted by modifying the components of the chiral manganese catalyst. This reaction demonstrates a wide substrate scope and achieves a turnover number of up to 107,800. Our mechanistic studies indicate that exceptional stereoselectivity arises from the modular assembly of confined chiral catalysts and cooperative non-covalent interactions between the catalyst and the substrate.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Estereoisomerismo / Técnicas de Química Sintética / Hidrogenación / Iminas / Nitrilos Idioma: En Revista: Nature Año: 2024 Tipo del documento: Article País de afiliación: China

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Estereoisomerismo / Técnicas de Química Sintética / Hidrogenación / Iminas / Nitrilos Idioma: En Revista: Nature Año: 2024 Tipo del documento: Article País de afiliación: China