e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
Tetrahedron
Experimental and DFT study of the conversion of ephedrine derivatives into oxazolidinones. Double SN 2 mechanism against SN 1 mechanism
A El Moncef, MA González, E Zaballos, RJ Zaragozá
Index: El Moncef, Abdelkarim; El Hadrami, El Mestafa; Gonzalez, Miguel A.; Zaballos, Elena; Zaragoza, Ramon J. Tetrahedron, 2010 , vol. 66, # 27-28 p. 5173 - 5184
Sulfonation of the N-Boc derivatives of 1, 2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and/or retention of configuration (threo derivatives) at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated by attack of the ...
