Catalytic multi-step domino and one-pot reactions

• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

• through concerted or stepwise mechanisms. An enantioselective palladium-catalyzed three-component reaction of glyoxylic acid, sulfonamides, and aryltrifluoroborates toward synthetically useful α-arylglycine compounds is described by the Manolikakes group [11]. Moreover, Šebesta and co-workers report a

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• and colleagues achieved a significant breakthrough by sequentially unveiling a series of decarboxylative alkylation reactions involving heteroarenes 22, enamides 24, N-arylglycine derivatives 26, and silyl enol ethers 28 [21][22]. Notably, these transformations were accomplished using only a catalytic

Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

• Bastian Jakob,
• Nico Schneider,
• Luca Gengenbach and
• Georg Manolikakes

Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52

• , sulfonamides and aryltrifluoroborates is described. This process provides modular access to the important α-arylglycine motif in moderate to good yields and enantioselectivies. The formed α-arylglycine products constitute useful building blocks for the synthesis of peptides or arylglycine-containing natural

• amino acids received increasing attention due to advances in protein-engineering and the development of protein-based therapeutics [3][4]. Among the different types of non-proteinogenic and unnatural amino acids, α-arylglycines play a particular important role. The arylglycine scaffold can be found in

• several well-known natural products with interesting biological properties, such as the glycopeptide antibiotics vancomycin and teicoplanin [5] or feglymycin [6], a 13mer peptide which contains nine α-arylglycines in its backbone. α-Arylglycine derivatives are used in the production of important drugs

Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

• Agnieszka Grajewska,
• Maria Chrzanowska and
• Wiktoria Adamska

Beilstein J. Org. Chem. 2021, 17, 2511–2519, doi:10.3762/bjoc.17.168

• -methylenedioxyphenylboronic acid (5c) reacted easily with aminoacetals 3b and 3a, respectively and glyoxylic acid hydrate (4), affording the corresponding arylglycine derivatives 6d and 6e, in satisfactory yields of 73% and 95%, respectively (Scheme 4). After cyclization in 20% HCl, compounds 6d and 6e were transformed into

Functionalization of N-arylglycine esters: electrocatalytic access to C–C bonds mediated by n-Bu₄NI

• Mi-Hai Luo,
• Yang-Ye Jiang,
• Kun Xu,
• Yong-Guo Liu,
• Bao-Guo Sun and
• Cheng-Chu Zeng

Beilstein J. Org. Chem. 2018, 14, 499–505, doi:10.3762/bjoc.14.35

• Business University, Beijing 100048, China 10.3762/bjoc.14.35 Abstract An efficient electrocatalytic functionalization of N-arylglycine esters is reported. The protocol proceeds in an undivided cell under constant current conditions employing the simple, cheap and readily available n-Bu4NI as the mediator

• electrochemical C–H bond functionalization, leading to the formation of new C–C, C–N, C–O and C–S bonds [28][29][30][31]. Herein, we report the electrochemical α-C–H functionalization of N-arylglycine esters with C–H nucleophiles using n-Bu4NI as redox catalyst (Scheme 1). The chemistry was performed in an

• undivided cell under constant current electrolysis. It was observed that n-Bu4NI promotes the reaction dramatically and higher yields of α-functionalized products were afforded compared with the direct electrolysis. Results and Discussion Initially, N-arylglycine ester 1a and C–H nucleophile 1,3,5

The chemistry of amine radical cations produced by visible light photoredox catalysis

• Jie Hu,
• Jiang Wang,
• Theresa H. Nguyen and
• Nan Zheng

Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234

• ] and Rueping [83] independently reported that N-arylglycine derivatives 65 are viable substrates (Scheme 16). They are presumably converted to imines 65a that are intercepted by indoles to give the Mannich-like adducts 67. The conditions used by Li were 10 mol % Ru(bpy)3Cl2 and 1 atm O2 at 40 °C with a

• 5 W blue LED as the light source. N-arylglycine derivatives 65, including esters and ketones, were successfully converted to the products 67. Rueping used Ir(ppy)2(bpy)PF6 as the photocatalyst, air, and an 11 W fluorescent bulb as the light source. Additionally, Zn(OAc)2 was employed as a Lewis acid

• cocatalyst. It was postulated that Zn(OAc)2 facilitates the conversion of the initially formed amine radical cation to the imine 65a and subsequently activates the imine for nucelophilic attack. N-arylglycine esters and N-arylglycine derived dipeptides worked quite well under these conditions. However, the

Arylglycine-derivative synthesis via oxidative sp³ C–H functionalization of α-amino esters

• Zhanwei Xu,
• Xiaoqiang Yu,
• Xiujuan Feng and
• Ming Bao

Beilstein J. Org. Chem. 2012, 8, 1564–1568, doi:10.3762/bjoc.8.178

• Zhanwei Xu Xiaoqiang Yu Xiujuan Feng Ming Bao State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, China 10.3762/bjoc.8.178 Abstract An efficient method for the synthesis of arylglycine derivatives is described. The oxidative coupling reactions of naphthols and

• phenols with α-amino esters proceeded smoothly in the presence of meta-chloroperoxybenzoic acid as an oxidant under ambient conditions, to produce arylglycine derivatives in satisfactory yields. Keywords: α-amino ester; arylglycine; C–H functionalization; oxidation; synthesis; Findings Arylglycine

• derivatives represent important synthetic intermediates or building blocks for drug development and natural-product synthesis [1][2]. The arylglycine moiety also occurs in several bioactive natural products [3]. Consequently, the development of convenient and efficient methods for the preparation of