Modular Synthesis of α‐Quaternary Chiral β‐Lactams via Three‐Component Asymmetric Kinugasa/Aldol or Kinugasa/Mannich Cascade Reactions

The β-lactam scaffolds are the prevalent structural units in antibiotics and natural products. Herein, three-component asymmetric Kinugasa/aldol and Kinugasa/Mannich cascade reactions have been developed for constructing α-quaternary chiral β-lactams. This method involved the tandem reaction of alkynes, nitrones and aldehydes (or imines), resulting in the formation of three sequential stereocenters controlled by copper(I) catalysts and chiral bis(oxazolidine) ligands. The developed protocol features high enantioselectivity, good reaction efficiency, and mild operational conditions, representing a practical and sustainable synthetic tool for the construction of functionalized chiral β-lactams.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-11-07
DOI
https://doi.org/10.1002/chem.202403722
Citations
3
Primary Topic
Synthesis of β-Lactam Compounds
Type
article
Field-Weighted Citation Impact
0.75

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article

Modular Synthesis of α‐Quaternary Chiral β‐Lactams via Three‐Component Asymmetric Kinugasa/Aldol or Kinugasa/Mannich Cascade Reactions

Linxuan Wang, Zhenghu Xu, Haoyu Li, Jialin Qi
3 citations
Chemistry - A European Journal
Synthesis of β-Lactam Compounds
0.75
article

Modular Synthesis of α‐Quaternary Chiral β‐Lactams via Three‐Component Asymmetric Kinugasa/Aldol or Kinugasa/Mannich Cascade Reactions

Linxuan Wang, Zhenghu Xu, Haoyu Li, Jialin Qi
article en
3 citations

Abstract

The β-lactam scaffolds are the prevalent structural units in antibiotics and natural products. Herein, three-component asymmetric Kinugasa/aldol and Kinugasa/Mannich cascade reactions have been developed for constructing α-quaternary chiral β-lactams. This method involved the tandem reaction of alkynes, nitrones and aldehydes (or imines), resulting in the formation of three sequential stereocenters controlled by copper(I) catalysts and chiral bis(oxazolidine) ligands. The developed protocol features high enantioselectivity, good reaction efficiency, and mild operational conditions, representing a practical and sustainable synthetic tool for the construction of functionalized chiral β-lactams.

Chemistry - A European JournalVol. 31(6)
Shandong University (CN), Chinese Academy of Sciences (CN), Centre of Excellence for Advanced Materials (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 31%
Synthesis of β-Lactam Compounds
0.75
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