65715-14-2Relevant academic research and scientific papers
Regioselective and stereoselective glycidic oxirane ring opening: A new entry to optically pure α-alkyl α-hydroxy β-amino acid derivatives
García Ruano, Jose L.,García Paredes, Cristina
, p. 5357 - 5361 (2007/10/03)
The BF3·OEt2 catalyzed oxirane ring opening of glycidic esters or amides with acetonitrile afforded the corresponding 2-oxazolines under very mild conditions in good yields. The reactions are completely regioselective (the nitrogen attacks the β-carbon) and stereoselective (with inversion of configuration) starting from 2-alkyl or 2,3-dialkyl glycidic derivatives, but the stereoselectivity is lost and the regioselectivity is completely inverted from 2-aryl derivatives. The 2-oxazolines obtained are readily hydrolyzed into β-amino, α-hydroxy esters or amides. (C) 2000 Elsevier Science Ltd.
