Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

• Kei Murakami and
• Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 278–302, doi:10.3762/bjoc.9.34

• allylmagnesiation of alkynyl sulfone. Copper-catalyzed four-component reaction of alkynyl sulfoxide with alkylzinc reagent, diiodomethane, and benzaldehyde. Rhodium-catalyzed reaction of aryl alkynyl ketones with arylzinc reagents. Allylmagnesiation of propargyl alcohol, which provides the anti-addition product

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

• Yan Sun,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2

• ] derivatives in moderate yields (Scheme 1a) [15]. In order to explore the generality of this four-component reaction, the reactivity of the other cyclic 1,3-diketones was also investigated. In an exploratory experiment, the four-component reaction of p-methoxyaniline, dimethyl acetylenedicarboxylate, 1-benzyl

The multicomponent approach to N-methyl peptides: total synthesis of antibacterial (–)-viridic acid and analogues

• Ricardo A. W. Neves Filho,
• Sebastian Stark,
• Bernhard Westermann and
• Ludger A. Wessjohann

Beilstein J. Org. Chem. 2012, 8, 2085–2090, doi:10.3762/bjoc.8.234

• strategies and affords the optically active natural product in 20% overall yield over six steps. A more economical approach with only four steps leads to the similarly active racemate by utilizing a Ugi four-component reaction (Ugi-4CR) as the key transformation. A small library of viridic acid analogues is

• a bidirectional sequence from the least- to the most-reactive amine (NMe-Val < H-Ant-OBn < H-Gly) to yield the protected tetrapeptide 2 (Scheme 1a). Alternatively, a multicomponent (MCR) approach based on a Ugi four-component reaction (Ugi-4CR) of dipeptide 3, isobutyraldehyde, methylamine and

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• another allenic unit. After a new transmetalation step with the boronic acid, the active catalytic species can be released and entered into a new catalytic cycle (Scheme 13). Imine as a nucleophilic partner A tandem four-component reaction allowing access to 1,2-dihydroisoquinolin-1-ylphosphonates 26 was

• -dihaloarene partner and the corresponding polysubstituted indoles were isolated in good yields as single regioisomers (Scheme 23). Based on this concept, Alper and coworkers reported the synthesis of isoindolin-1-one derivatives 53 through a four-component reaction starting from ortho-dihaloarenes and

• stereoselectivity. A four-component reaction was further developed through an in situ post C–B arylation by adding a second aryl iodide, with Cs2CO3 and water, to the newly formed alkenylboronate 78. The subsequent Suzuki–Miyaura coupling led to the formation of 2,3-diarylated amines 79 and the best results were

Novel synthesis of pseudopeptides bearing a difluoromethyl group by Ugi reaction and desulfanylation

• Jingjing Wu,
• Hui Li and
• Song Cao

Beilstein J. Org. Chem. 2011, 7, 1070–1074, doi:10.3762/bjoc.7.123

• triglyceride transfer protein (MTP) and useful for the treatment of obesity and atherosclerosis (Figure 1) [20]. Among the protocols for the preparation of pseudopeptide derivatives, the Ugi four-component reaction offers significant advantages over conventional linear-step synthesis [21]. Various fluorinated

• building blocks have been used in the Ugi four-component reaction to construct a fluorinated compound library [22][23][24][25]. Our group has always been interested in developing efficient methods for the preparation of difluoromethyl-containing compounds through multicomponent reactions [26][27][28][29

Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium- catalyzed intramolecular C-H functionalization

• Florence Bonnaterre,
• Michèle Bois-Choussy and
• Jieping Zhu

Beilstein J. Org. Chem. 2008, 4, No. 10, doi:10.3762/bjoc.4.10

• . Introduction Multicomponent reactions (MCRs) offer a unique way to generate efficiently libraries of complex molecules with high degree of diversity [1][2]. Among them, the Ugi four component reaction (Ugi-4CR) is without doubt one of the most powerful transformations that has been extensively investigated for

• Scheme 1. The Ugi four-component reaction between an o-iodobenzaldehyde 2, an aniline 3, an isocyanide 4 and a carboxylic acid 5 should afford an α-acetamido-α-phenylacetamide 6, which upon palladium-catalyzed C-H activation process should provide dihydrophenanthridine 1 [15][16][17][18][19][20][21

• developed an efficient palladium-catalyzed intramolecular CH-arylation reaction leading, under ligandless conditions, to dihydrophenanthridines in good to excellent yields. In combination with the Ugi four-component reaction, this medicinally important heterocycle can be easily prepared in two steps from