García-Mingüens, Eduardo, Ferrándiz-Saperas, Marcos, Retamosa, Maria de Gracia, Nájera, Carmen, Yus, Miguel, Sansano, Jose M.
Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines
García-Mingüens E, Ferrándiz-Saperas M, de Gracia Retamosa M, Nájera C, Yus M, Sansano JM. Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines. Molecules. 2022; 27(14):4579. https://doi.org/10.3390/molecules27144579
URI: http://hdl.handle.net/10045/126189
DOI: 10.3390/molecules27144579
ISSN: 1420-3049
Abstract: 
The enantioselective 1,3-dipolar cycloaddition between imino esters and (Z)-nitroalkenes bearing a masked amino group in the β-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly applied to the study of the scope of the reaction. The determination of the absolute configuration was evaluated using NMR experiments and electronic circular dichroism (ECD). The reduction and hydrolysis of both groups was performed to generate in an excellent enantiomeric ratio the corresponding cis-2,3-diaminoprolinate.
Keywords:Nitroprolinates, Enantioseletive cycloaddition, Phosphoramidite, Azomethine ylides, Diamines
MDPI
info:eu-repo/semantics/article