{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["15(26)"],"submitter":["Liu JH"],"pubmed_abstract":["Despite the long-standing exploration of the catalytic asymmetric Tsuji-Trost allylation reaction since the mid-20th century, most reported instances have adhered to a two-component approach. Here, we present a remarkably efficient three-component asymmetric allylation reaction enabled by the collaborative action of chiral aldehyde and palladium. A diverse array of NH<sub>2</sub>-unprotected amino acid esters, aryl or alkenyl iodides, and allyl alcohol esters exhibit robust participation in this reaction, resulting in the synthesis of structurally diverse non-proteinogenic α-amino acid esters with favorable experimental outcomes. Mechanistic investigations reveal the dominance of the allylation/Heck coupling cascade in reactions involving electron-rich aryl iodides, while the Heck coupling/allylation cascade emerges as the dominant pathway in reactions involving electron-deficient aryl iodides. This chiral aldehyde/palladium combining catalytic system precisely governs the chemoselectivity of <i>C</i>-allylation and <i>N</i>-allylation, the regioselectivity of linear and branched allylation, and the enantioselectivity of <i>C</i>-allylation products."],"journal":["Chemical science"],"pagination":["10232-10236"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11220596"],"repository":["biostudies-literature"],"pubmed_title":["Asymmetric three-component Tsuji-Trost allylation reaction enabled by chiral aldehyde/palladium combined catalysis."],"pmcid":["PMC11220596"],"pubmed_authors":["Cai T","Huang YM","Liu JH","Wu ZL","Guo QX","Wen W"],"additional_accession":[]},"is_claimable":false,"name":"Asymmetric three-component Tsuji-Trost allylation reaction enabled by chiral aldehyde/palladium combined catalysis.","description":"Despite the long-standing exploration of the catalytic asymmetric Tsuji-Trost allylation reaction since the mid-20th century, most reported instances have adhered to a two-component approach. Here, we present a remarkably efficient three-component asymmetric allylation reaction enabled by the collaborative action of chiral aldehyde and palladium. A diverse array of NH<sub>2</sub>-unprotected amino acid esters, aryl or alkenyl iodides, and allyl alcohol esters exhibit robust participation in this reaction, resulting in the synthesis of structurally diverse non-proteinogenic α-amino acid esters with favorable experimental outcomes. Mechanistic investigations reveal the dominance of the allylation/Heck coupling cascade in reactions involving electron-rich aryl iodides, while the Heck coupling/allylation cascade emerges as the dominant pathway in reactions involving electron-deficient aryl iodides. This chiral aldehyde/palladium combining catalytic system precisely governs the chemoselectivity of <i>C</i>-allylation and <i>N</i>-allylation, the regioselectivity of linear and branched allylation, and the enantioselectivity of <i>C</i>-allylation products.","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Jul","modification":"2025-04-22T12:08:16.716Z","creation":"2025-04-06T00:13:01.922Z"},"accession":"S-EPMC11220596","cross_references":{"pubmed":["38966351"],"doi":["10.1039/d4sc02594f"]}}