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Imidazoline‐Proline and Imidazoline‐Prolinate Ligands for Copper‐Catalyzed Asymmetric Exo‐Selective 3 + 2 Cycloaddition of Iminoesters with Nitroalkenes
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Imidazoline‐Proline and Imidazoline‐Prolinate Ligands for Copper‐Catalyzed Asymmetric Exo‐Selective 3 + 2 Cycloaddition of Iminoesters with Nitroalkenes
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Imidazoline‐Proline and Imidazoline‐Prolinate Ligands for Copper‐Catalyzed Asymmetric Exo‐Selective 3 + 2 Cycloaddition of Iminoesters with Nitroalkenes
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Journal Article
Imidazoline‐Proline and Imidazoline‐Prolinate Ligands for Copper‐Catalyzed Asymmetric Exo‐Selective 3 + 2 Cycloaddition of Iminoesters with Nitroalkenes
2026
Overview
Diphenylethylenediamine‐derived imidazoline‐amino acid derivatives are designed as nonphosphine chiral nitrogen ligands for metal‐catalyzed exo‐selective [3 + 2] cycloaddition reaction of iminoesters with nitroalkenes. The newly developed (R,R)‐imidazoline‐L‐proline and t‐butyl prolinate‐Cu(OTf)2 complexes afford the exo‐pyrrolidine adducts with up to 99% ee. From a modular synthesis of nonphosphine chiral nitrogen‐based chiral imidazoline–amino acid ligands, two new chiral imidazoline–proline‐copper catalysts are developed for targeting exo‐selective [3 + 2] cycloaddition reaction. Density functional theory studies rationalize the observed stereoselectivity and the distinct chiral pockets of the two catalysts account for their different substrate compatibility.
Publisher
Wiley-VCH
Subject
