159406-31-2Relevant academic research and scientific papers
Diastereoselective Amidoalkylation Reactions of Electrochemically Methoxylated Chiral 2-Oxazolidinones with Organocopper Reagents
Zietlow, Andrea,Steckhan, Eberhard
, p. 5658 - 5661 (1994)
(4RS,5R)-4-Methoxy-5-methyl-2-oxazolidinone (2ab), easily obtained by electrochemical decarboxylative methoxylation of the cyclic L-threonine derivative (4S,5R)-5-methyl-2-oxazolidinone-4-carboxylic acid (1), acts as effective diastereoselective amidoalkylation reagent.The methoxy group exchange in 2ab can be performed with higher order organocuprates (R3Cu2Li) in the presence of BF3*OEt2.The 4-alkyl- or 4-aryl-substituted 2-oxazolidinones 3-6 can be obtained with trans diastereoselectivities between 75 and 98percent in SN1 fashion via the intermediate N-acylimine.On the contrary, the N-methylated (4RS,5R)-4-methoxy-3,5-dimethyl-2-oxazolidinone (7ab) undergoes methoxy group exchange under identical conditions mainly via the SN2 mechanism.Thus, starting from trans-7a mainly cis-8b is formed with 76percent ds.The described procedures make cis- or trans-4-alkyl-5-methyl-2-oxazolidinones and the respective dichiral 2-amino alcohols selectively available by a short reaction sequence.
3-PYRIMIDIN-4-YL-OXAZOLIDIN-2-ONES AS INHIBITORS OF MUTANT IDH
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Paragraph 0261; 0262, (2014/09/03)
The invention is directed to a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1-R6 are defined herein. The invention is also directed to compositions containing a compound of formula (I) and to the use of such compounds in the inhibition of mutant IDH proteins having a neomorphic activity. The invention is further directed to the use of a compound of formula (I) in the treatment of diseases or disorders associated with such mutant IDH proteins including, but not limited to, cell-proliferation disorders, such as cancer.
Examining the origin of selectivity in the reaction of racemic alcohols with chiral N-phosphoryl oxazolidinones
Crook, Samuel,Parr, Nigel J.,Simmons, Jonathan,Jones, Simon
, p. 1298 - 1308 (2015/01/09)
A range of known and novel N-phosphoryl oxazolidinones and imidazolidinones were prepared and screened in the kinetic resolution of a range of racemic magnesium chloroalkoxides. Models are proposed to account for the enantioselectivity achieved based on a combination of chiral relay effects, generation of transient stereochemistry and the structure of the intermediate magnesium alkoxide.
3-PYRIMIDIN-4-YL-OXAZOLIDIN-2-ONES AS INHIBITORS OF MUTANT IDH
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Page/Page column 46-48, (2013/04/13)
The invention is directed to a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1-R6 are defined herein. The invention is also directed to compositions containing a compound of formula (I) and to the use of such compounds in the inhibition of mutant IDH proteins having a neomorphic activity. The invention is further directed to the use of a compound of formual (I) in the treatment of diseases or disorders associated with such mutant IDH proteins including, but not limited to, cell-proliferation disorders, such as cancer
