Facial Selectivity in Mechanical Bond Formation : Axially Chiral Enantiomers and Geometric Isomers from a Simple Prochiral Macrocycle
In 1971, Schill recognized that a prochiral macrocycle encircling an oriented axle led to geometric isomerism in rotaxanes. More recently, we identified an overlooked chiral stereogenic unit in rotaxanes that arises when a prochiral macrocycle encircles a prochiral axle. Here, we show that both stereogenic units can be accessed using equivalent strategies, with a single weak stereodifferentiating interaction sufficient for moderate to excellent stereoselectivity. Using this understanding, we demonstrated the first direct enantioselective (70% ee) synthesis of a mechanically axially chiral rotaxane.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:146 |
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| Enthalten in: |
Journal of the American Chemical Society - 146(2024), 13 vom: 03. Apr., Seite 9134-9141 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Gallagher, Peter R [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 07.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/jacs.3c14329 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a In 1971, Schill recognized that a prochiral macrocycle encircling an oriented axle led to geometric isomerism in rotaxanes. More recently, we identified an overlooked chiral stereogenic unit in rotaxanes that arises when a prochiral macrocycle encircles a prochiral axle. Here, we show that both stereogenic units can be accessed using equivalent strategies, with a single weak stereodifferentiating interaction sufficient for moderate to excellent stereoselectivity. Using this understanding, we demonstrated the first direct enantioselective (70% ee) synthesis of a mechanically axially chiral rotaxane | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Savoini, Andrea |e verfasserin |4 aut | |
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| 700 | 1 | |a Maynard, John R J |e verfasserin |4 aut | |
| 700 | 1 | |a Butler, Patrick W V |e verfasserin |4 aut | |
| 700 | 1 | |a Tizzard, Graham J |e verfasserin |4 aut | |
| 700 | 1 | |a Goldup, Stephen M |e verfasserin |4 aut | |
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