29218-27-7Relevant articles and documents
Corrigendum to: Substrate-Controlled Product Divergence: Conversion of CO2into Heterocyclic Products (Angew. Chem. Int. Ed., (2016), 55, (3972–3976) 10.1002/anie.201511521)
Rintjema, Jeroen,Epping, Roel,Fiorani, Giulia,Martín, Eddy,Escudero-Adán, Eduardo C.,Kleij, Arjan W.
, p. 12136 - 12136 (2016)
Figure 2 of this Communication needs to be revised as shown below. Specifically, compounds 18 and 19 were erroneously exchanged from their position. The authors wish to apologize for this error. (Figure presented.).
Microwave-Assisted Electrostatically Enhanced Phenol-Catalyzed Synthesis of Oxazolidinones
Al-Harrasi, Ahmed,Ebrahimi, Amirhossein,Golmohammadi, Farhad,Rostami, Ali,Sakhaee, Nader
, (2021/10/20)
An electrostatically enhanced phenol is utilized as a straightforward, sustainable, and potent one-component organocatalyst for the atom-economic transformation of epoxides to oxazolidinones under microwave irradiation. Integrating a positively charged center into phenols over a modular one-step preparation gives rise to a bifunctional system with improved acidity and activity, competent in rapid assembly of epoxides and isocyanates under microwave irradiation in a short reaction time (20-60 min). A careful assessment of the efficacy of various positively charged phenols and anilines and the impact of several factors, such as catalyst loading, temperature, and the kind of nucleophile, on catalytic reactivity were examined. Under neat conditions, this one-component catalytic platform was exploited to prepare more than 40 examples of oxazolidinones from a variety of aryl- and alkyl-substituted epoxides and isocyanates within minutes, where up to 96% yield and high degree of selectivity were attained. DFT calculations to achieve reaction barriers for different catalytic routes were conducted to provide mechanistic understanding and corroborated the experimental findings in which concurrent epoxide ring-opening and isocyanate incorporation were proposed.
Synthesis of Oxazolidinones by using Carbon Dioxide as a C1 Building Block and an Aluminium-Based Catalyst
Sengoden, Mani,North, Michael,Whitwood, Adrian C.
, p. 3296 - 3303 (2019/07/05)
Oxazolidinone synthesis through the coupling of carbon dioxide and aziridines was catalysed by an aluminium(salphen) complex at 50–100 °C and 1–10 bar pressure under solvent-free conditions. The process was applicable to a variety of substituted aziridines, giving products with high regioselectivity. It involved the use of a sustainable and reusable aluminium-based catalyst, used carbon dioxide as a C1 source and provided access to pharmaceutically important oxazolidinones as illustrated by a total synthesis of toloxatone. This protocol was scalable, and the catalyst could be recovered and reused. A catalytic cycle was proposed based on stereochemical, kinetic and Hammett studies.
