58628-98-1Relevant academic research and scientific papers
(Enantio)selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols
Pe?a-López, Miguel,Neumann, Helfried,Beller, Matthias
supporting information, p. 7826 - 7830 (2016/07/07)
A novel strategy for the synthesis of oxazolidin-2-ones from vicinal diols and urea is described. In this heterocycle synthesis, two different C?O and C?N bonds are sequentially formed in a domino process consisting of nucleophilic substitution and alcohol amination. The use of readily available starting materials and the good atom economy render this process environmentally benign. While this transformation is already highly chemo- and regioselective, we also developed the first asymmetric version of this method using (R)-(+)-MeO-BIPHEP as the chiral ligand.
Aluminium-Catalysed Oxazolidinone Synthesis and their Conversion into Functional Non-Symmetrical Ureas
Laserna, Victor,Guo, Wusheng,Kleij, Arjan W.
, p. 2849 - 2854 (2015/09/28)
An efficient and practical aluminium-catalysed approach towards a range of functional oxazolidinones is reported. The method is based on cheap and readily available starting materials including terminal and internal (bicyclic) epoxides and phenyl carbamate. The oxazolidinones serve as highly useful synthons for the high yield preparation of non-symmetrical ureas by nucleophilic ring-opening affording the targeted urea compounds with excellent functional group diversity, high regioselectivity and isolated yields up to >99%.
Synthesis of 2-oxazolidinones from CO2 and 1,2-aminoalcohols catalyzed by n-Bu2SnO
Tominaga, Ken-Ichi,Sasaki, Yoshiyuki
, p. 307 - 309 (2007/10/03)
The dehydrative condensation of 1,2-aminoalcohols with CO2 is found to proceed in NMP as solvent; 2-oxazolidinones are obtained in the yields of 53-94% when a commercially available tin compound, n-Bu2SnO is used as catalyst.
A short diastereo- and enantioselective synthesis of cis-4,5-disubstituted oxazolidin-2-ones
Enders,Kallfass,Nolte
, p. 33 - 36 (2007/10/03)
The asymmetric synthesis of cis-4,5-disubstituted oxazolidin-2-ones is described. Following a four step reaction sequence of α-alkylation, 1,2-addition with subsequent carbamate protection, cyclization and concluding with cleavage of the auxiliary the title compounds are obtained in moderate yields and in excellent diastereo- and enantiomeric excesses (de = 88 - > 96%, ee > 96%).
