Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

• James Guevara-Pulido,
• Fernando González-Pérez,
• José M. Andrés and
• Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

• organometallic catalysis [15], enzymatic catalysis [16], aminocatalysis [17][18][19], and hydrogen-bonding catalysis [20][21][22]. The Michael addition reaction is a versatile synthetic methodology that allows the formation of new carbon–carbon and carbon–heteroatom bonds through the coupling of electron-poor

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal

• Alessandro Brusa,
• Debora Iapadre,
• Maria Edith Casacchia,
• Alessio Carioscia,
• Giuliana Giorgianni,
• Giandomenico Magagnano,
• Fabio Pesciaioli and
• Armando Carlone

Beilstein J. Org. Chem. 2023, 19, 1243–1250, doi:10.3762/bjoc.19.92

• single operation and from readily available substrates. Their combination with asymmetric aminocatalysis [4][6][7][8] has recently led to innovative approaches for the one-step enantioselective preparation of stereochemically dense molecules. Nowadays, organocatalytic cascade processes provide a powerful

• complete enantiocontrol (Scheme 1). This elegantly designed example established a new direction in asymmetric aminocatalysis, leading to an impressive growth of methods based on organocascade processes [8][10][13][14][15][16]. The experimental simplicity of the strategy offers the potential of rapidly

• self-aldol condensations, polymerization and Tishchenko-type processes) and stereoselectivity [20]; the activation of acetaldehyde via aminocatalysis, furthermore, suffers from a lack of proper steric hindrance for the enantio-discrimination process. However, some methodologies enabling the use of

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

• Alejandro Castán,
• Ramón Badorrey,
• José A. Gálvez and
• María D. Díaz-de-Villegas

Beilstein J. Org. Chem. 2017, 13, 612–619, doi:10.3762/bjoc.13.59

• privileged motif [5] with a powerful capacity in aminocatalysis [6][7][8][9][10]. In this context diarylprolinol silyl ethers have proven to be extremely efficient organocatalysts for a wide variety of chemical transformations [11]. In the course of our research we have been involved in the synthesis of new

• nitroolefins was selected as a model reaction to evaluate the effectiveness of the new pyrrolidine-based organocatalysts in aminocatalysis. Results and Discussion We reasoned that pyrrolidines of type C with a bulky 2,2-disubstituted-1,3-dioxolan-4-yl moiety at C2 could provide the appropriate environment to

The aminoindanol core as a key scaffold in bifunctional organocatalysts

• Isaac G. Sonsona,
• Eugenia Marqués-López and
• Raquel P. Herrera

Beilstein J. Org. Chem. 2016, 12, 505–523, doi:10.3762/bjoc.12.50

• incorporated into proline derivatives has been scarcely explored. Herein, the most representative and illustrative examples are compiled and this review will be mainly focused on the cases where the aminoindanol moiety confers bifunctionality to the organocatalysts. Keywords: aminocatalysis; 1,2-aminoindanol

• enantioselectivity. Aminocatalysis Although aminoindanol-derived catalysts have been scarcely used in aminocatalysis, some relevant examples have been found in the literature, especially in the enantioselective addition of ketones to nitroalkene compounds. In this context, Alonso, Nájera and co-workers designed

• . Diels–Alder reaction catalyzed by the aminoindanol derivative ent-41. Asymmetric Michael addition of 3-pentanone (55a) to the nitroalkenes 3 through aminocatalysis. Substrate scope extension for the asymmetric Michael addition between the ketones 55 and the nitroalkenes 3 through aminocatalysis. A

Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions

• Matthias Leven,
• Jörg M. Neudörfl and
• Bernd Goldfuss

Beilstein J. Org. Chem. 2013, 9, 155–165, doi:10.3762/bjoc.9.18

• catalysis provides an effective alternative to conventional primary amino catalysis were strong acid additives are essential components. Keywords: alkali metals; aminocatalysis; DFT-calculations; Lewis acids; Michael addition; Introduction Organocatalysis based on primary or secondary amines enables a