217311-57-4Relevant academic research and scientific papers
A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones
Bertau,Buerli,Hungerbuehler,Wagner
, p. 2103 - 2107 (2007/10/03)
A novel highly stereoselective synthesis of chiral mono- and bicyclic 4- and 4,5-substituted 2-oxazolidinones starting from β-keto esters was developed. After bioreduction with S. cerevisiae the resulting homochiral β-hydroxy esters are transformed into their hydrazides. Treatment with NaNO2/H+ then furnishes 2-oxazolidinones in high e.e. (～99%) and d.e. (>99%). The ring formation proceeds via a highly concerted sextet rearrangement with full retention of configuration at the stereocentres. Enantiopure 1,2-amino alcohols can subsequently be obtained by saponification of the 2-oxazolidinone products.
