Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines

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