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

文献索引：El Moncef, Abdelkarim; El Hadrami, El Mestafa; Gonzalez, Miguel A.; Zaballos, Elena; Zaragoza, Ramon J. Tetrahedron, 2010 , vol. 66, # 27-28 p. 5173 - 5184

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被引用次数: 6

摘要

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 ...