An iron-catalysed radical cyclization/C(sp3)–H alkylation cascade between γ, δ-unsaturated oxime esters and glycine derivatives: access to pyrroline-containing amino acids. Issue 2 (1st December 2022)

• Record Type: Journal Article
• Authors: Yu, Fangyuan; Yang, Sen; Xie, Zihao; Lu, Dengfu; Gong, Yuefa
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 2(2023)
• Page Start: 382
• Page End: 387
• Publication Date: 2022-12-01
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01543a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An iron-catalysed and ligand-controlled selective α-C–H alkylation of N -aryl glycinates is established with γ, δ-unsaturated oxime esters as the reagent. This method provides a facile synthetic approach to obtain pyrroline-containing amino acids. Abstract : An iron-catalysed selective C(sp 3 ) –H alkylation method for glycine derivatives is reported. Using γ, δ-unsaturated oxime esters as both the alkylation reagent and terminal oxidant, N -aryl glycinates could be converted into a series of pyrroline-containing amino esters with a readily available iron catalyst and a phenanthroline-based ligand. Control experiments showed that the ligand plays a key role in tuning the chemoselectivity, while a radical–polar crossover pathway is proposed according to the mechanistic studies. Additionally, the products obtained with this method could be transformed into various valuable building blocks, including amino acids, amino alcohols and γ-lactams.