114364-42-0Relevant articles and documents
Organotellurium-mediated Synthesis of Oxazolidin-2-ones from Alkenes
Hu, Nan X.,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
, p. 1447 - 1448 (1987)
Phenyltellurinyl trifluoroacetate in combination with ethyl carbamate and boron trifluoride-diethyl ether reacted with alkenes in refluxed 1,2-dichloroethane, regio- and stereo-selectively giving oxazolidin-2-ones in high yields.
Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions
Chang, Sukbok,Jung, Hoimin,Kim, Dongwook,Lee, Jeonghyo,Lee, Jia,Park, Juhyeon
supporting information, p. 12324 - 12332 (2020/08/06)
Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.
Interaction of substrate and catalyst during the formation of oxazolidinones from 2-aminoalcohols and diethyl carbonate using recyclable 1,3-dichlorodistannoxanes
Pulla, Sharon,Unnikrishnan, Vineed,Ramidi, Punnamchandar,Sullivan, Shane Z.,Ghosh, Anindya,Dallas, Jerry L.,Munshi, Pradip
experimental part, p. 33 - 43 (2011/05/02)
An efficient synthesis of oxazolidinone (OXZ) using 2-aminoalcohols (2AAs) and diethyl carbonate (DEC) as reagents in the presence of recyclable catalyst 1,3-dichloro-1,1,3,3-tetraalkyldistannoxane, [(RR′SnCl)2O] 2 (1) is reported. 0.5 mol% (with respect to 2AA) of 1 provides OXZ quantitatively within 1 h at 80 °C with turnover frequency (TOF) of 200 h-1. The observed TOF is much higher than the reported value (4 h-1) of the most convenient and commercially feasible K 2CO3 catalyst. Chiral 2AAs produce OXZs with 99% ee. Molar dependency of 1, DEC and 2AA is found to be 1:2:2. Molar conductivities (Ω-1 cm2 mol-1) in DMSO at 25 °C are 6.41 for 1a (R = R′ = Bu), 5.25 for 1b (R = Bu, R′ = Ph), 2.87 for 1c (R = Ph, R′ = Bu), and 2.21 for 1d (R = R′ = Ph) which reveal the mobility of bridged Cl in 1 during reaction. The study of a broad range of substrates and reaction parameters supports a reaction pathway that begins with initial attack by -OH of the pre-formed 2-ethylcarbamato aminoalcohol (2ECA) of 2AA on Snb of 1 displacing the bridged Cl. Change in the reaction rates resulted due to various alkyl and aryl substituents on Sn provides better understanding of the distannoxane catalysis, which has not been attempted before for the said reaction.