ArticleAngewandte Chemie (International ed. in English)2022
Ring-to-Thread Chirality Transfer in [2]Rotaxanes for the Synthesis of Enantioenriched Lactams.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Spatial Assembly of Mechanically Planar Chiral Rotaxanes on Rationally Designed Cavitands.Angewandte Chemie (International ed. in English) · 2025Article
- A Thiourea-Based Rotaxane Catalyst: Nucleophilic Fluorination Phase-Transfer Process Unlocked by the Mechanical Bond.Organic letters · 2025Article
- Facial Selectivity in Mechanical Bond Formation: Axially Chiral Enantiomers and Geometric Isomers from a Simple Prochiral Macrocycle.Journal of the American Chemical Society · 2024Article
- Kinetically controlled synthesis of rotaxane geometric isomers.Chemical science · 2024Article
- Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes.Journal of the American Chemical Society · 2024Article
- Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures.Beilstein journal of organic chemistry · 2024Review
- Recent Advances in the Preparation of Delivery Systems for the Controlled Release of Scents.International journal of molecular sciences · 2023Review
- Ring-to-Thread Chirality Transfer in [2]Rotaxanes for the Synthesis of Enantioenriched Lactams.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The synthesis of chiral mechanically interlocked molecules has attracted a lot of attention in the last few years, with applications in different fields, such as asymmetric catalysis or sensing. Herein we describe the synthesis of orientational mechanostereoisomers, which include a benzylic amide macrocycle with a stereogenic center, and nonsymmetric N-(arylmethyl)fumaramides as the axis. The base-promoted cyclization of the initial fumaramide thread allows enantioenriched value-added compounds, such as lactams of different ring sizes and amino acids, to be obtained. The chiral information is effectively transmitted across the mechanical bond from the encircling ring to the interlocked lactam. High levels of enantioselectivity and full control of the regioselectivity of the final cyclic compounds are attained.
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