Stereoselective synthesis of δ-fluorinated isoleucines exploiting consecutive C(sp3)-H bond activations. (13th August 2022)

• Record Type: Journal Article
• Authors: Borgini, Matteo; Wipf, Peter
• Is Part Of: Tetrahedron. Volume 120(2022)
• Publication Date: 2022-08-13
• Subjects: C, H-bond activation -- Fluorinated amino acids -- Isoleucine -- Deprotection -- Palladium catalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132876
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Fluorinated α-amino acids are important building blocks for pharmaceutical and agrochemical industries, as well as in protein NMR and material science. We optimized a synthetic route to generate 5-fluoro-l -isoleucine (1 ) and 5, 5-difluoro-l -isoleucine (2 ) from l -alanine by leveraging two consecutive C(sp3)-H bond functionalization reactions and developed a new oxidation protocol to facilitate directing and protecting group removal without α-epimerization of the amino acid or trigger other side reactions. Graphical abstract: To create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions should not be changed or altered. Image 1