30414-58-5Relevant articles and documents
Synthesis of (1H-1,2,3-Triazol-1-yl)acetic Acid Derivatives
Obushak, M. D.,Pokhodylo, N. T.,Savka, R. D.
, p. 1421 - 1431 (2020/10/02)
Abstract: A convenient synthetic approach to (1H-1,2,3-triazol-1-yl)acetic acid derivatives via the reaction of azidoacetamides with β-ketoesters and acetylacetone is proposed. Based on this strategy, 1,5-disubstituted 1,2,3-triazoles were prepared from available reagents under metal-free conditions. A one-pot protocol for the synthesis of (5-methyl-1H-1,2,3-triazol-1-yl)acetamides derived from N-substituted chloroacetamides is developed.
Chiral Vanadyl(V) Complexes Enable Efficient Asymmetric Reduction of β-Ketoamides: Application toward (S)-Duloxetine
Chen, Chien-Tien,Maity, Nabin Ch.,Agarwal, Rachit,Lai, Chien-Fu,Liao, Yiya,Yu, Wei-Ru
supporting information, p. 6408 - 6419 (2020/07/14)
High-valent chiral oxidovanadium(V) complexes derived from 3,5-substituted-N-salicylidene-l-tert-leucine were used as catalysts in asymmetric reduction of N-benzyl-β-ketoamides. Among six different solvents, three different alcohol additives, and two different boranes examined, the use of pinacolborane in tetrahydrofuran (THF) with a t-BuOH additive led to the best results at -20 °C. The corresponding β-hydroxyamides can be furnished with yields up to 92percent and an enantiomeric excess (ee) up to 99percent. We have successfully extended this catalytic protocol for the synthesis of an (S)-duloxetine precursor.
Mechanistic studies on the CAN-mediated intramolecular cyclization of δ-aryl-β-dicarbonyl compounds
Casey, Brian M.,Sadasivam, Dhandapani V.,Flowers II, Robert A.
, p. 1472 - 1479 (2013/08/23)
The synthesis of 2-tetralones through the cyclization of δ-aryl-β-dicarbonyl substrates by using CAN is described. Appropriately functionalized aromatic substrates undergo intramolecular cyclizations generating 2-tetralone derivatives in moderate to good yields. DFT computational studies indicate that successful formation of 2-tetralones from δ-aryl-β-dicarbonyl radicals is dependent on the stability of the subsequent cyclohexadienyl radical intermediates. Furthermore, DFT computational studies were used to rationalize the observed site selectivity in the 2-tetralone products.
