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

Autor: Fu C; College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China., He L; College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China., Chang X; College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China., Cheng X; College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China., Wang ZF; College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China., Zhang Z; College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China., Larionov VA; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, 119334, Russian Federation.; Peoples' Friendship University of Russia, Moscow, 117198, Russian Federation., Dong XQ; College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China., Wang CJ; College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.; State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, China.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Feb 12; Vol. 63 (7), pp. e202315325. Date of Electronic Publication: 2024 Jan 12.
DOI: 10.1002/anie.202315325
Abstrakt: An 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.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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