1374824-06-2Relevant academic research and scientific papers
Catalytic enantioselective protonation of nitronates utilizing an organocatalyst chiral only at sulfur
Kimmel, Kyle L.,Weaver, Jimmie D.,Lee, Melissa,Ellman, Jonathan A.
supporting information; experimental part, p. 9058 - 9061 (2012/07/14)
The highly enantioselective protonation of nitronates formed upon the addition of α-substituted Meldrums acids to terminally unsubstituted nitroalkenes is described. This work represents the first enantioselective catalytic addition of any type of nucleophile to this class of nitroalkenes. Moreover, for the successful implementation of this method, a new type of N-sulfinyl urea catalyst with chirality residing only at the sulfinyl group was developed, thereby enabling the incorporation of a diverse range of achiral diamine motifs. Finally, the Meldrums acid addition products were readily converted to pharmaceutically relevant 3,5-disubstituted pyrrolidinones in high yield.
