Imidazoline‐Proline and Imidazoline‐Prolinate Ligands for Copper‐Catalyzed Asymmetric <i>Exo</i> ‐Selective [3 + 2] Cycloaddition of Iminoesters with Nitroalkenes

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.

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Publication Details

Journal
ChemistryEurope
Published
2025-09-04
DOI
https://doi.org/10.1002/ceur.202500260
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.00
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article

Imidazoline‐Proline and Imidazoline‐Prolinate Ligands for Copper‐Catalyzed Asymmetric Exo ‐Selective [3 + 2] Cycloaddition of Iminoesters with Nitroalkenes

Chihiro Tokumitsu, Takuya SHIMADA, Takayoshi Arai, Yan Yu et al.
ChemistryEurope
Asymmetric Synthesis and Catalysis
article

Imidazoline‐Proline and Imidazoline‐Prolinate Ligands for Copper‐Catalyzed Asymmetric Exo ‐Selective [3 + 2] Cycloaddition of Iminoesters with Nitroalkenes

Chihiro Tokumitsu, Takuya SHIMADA, Takayoshi Arai, Yan Yu, Allan N. Fujiwara
article en

Abstract

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.

ChemistryEuropeVol. 4(1)
Chiba University (JP)
Openalex Percentile: Top 82%
Asymmetric Synthesis and Catalysis
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