Copper/Ruthenium Relay Catalysis for Stereodivergent Access to δ‐Hydroxy α‐Amino Acids and Small Peptides

Author:

Fu Cong1,He Ling1,Chang Xin1,Cheng Xiang1,Wang Zuo‐Fei1,Zhang Zongpeng1,Larionov Vladimir A.23,Dong Xiu‐Qin1,Wang Chun‐Jiang14ORCID

Affiliation:

1. College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 China

2. A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences Moscow 119334 Russian Federation

3. Peoples' Friendship University of Russia Moscow 117198 Russian Federation

4. State Key Laboratory of Elemento-organic Chemistry Nankai University Tianjin 300071 China

Abstract

AbstractAn atom‐ and step‐economical and redox‐neutral cascade reaction enabled by asymmetric bimetallic relay catalysis by merging a ruthenium‐catalyzed asymmetric borrowing‐hydrogen reaction with copper‐catalyzed asymmetric Michael addition has been realized. A variety of highly functionalized 2‐amino‐5‐hydroxyvaleric acid esters or peptides bearing 1,4‐non‐adjacent stereogenic centers have been prepared in high yields with excellent enantio‐ and diastereoselectivity. Judicious selection and rational modification of the Ru catalysts with careful tuning of the reaction conditions played a pivotal role in stereoselectivity control as well as attenuating undesired α‐epimerization, thus enabling a full complement of all four stereoisomers that were otherwise inaccessible in previous work. Concise asymmetric stereodivergent synthesis of the key intermediates for biologically important chiral molecules further showcases the synthetic utility of this methodology.

Funder

National Key Research and Development Program of China

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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