Dirhodium Carboxylate Catalysts from 2-Fenchyloxy or 2-Menthyloxy Arylacetic Acids : Enantioselective C-H Insertion, Aromatic Addition and Oxonium Ylide Formation/Rearrangement
© 2021 The Authors. ChemCatChem published by Wiley-VCH GmbH..
A new class of dirhodium carboxylate catalysts have been designed and synthesized from 2-fenchyloxy or 2-menthyloxy arylacetic acids which display excellent enantioselectivity across a range of transformations of α-diazocarbonyl compounds. The catalysts were successfully applied to enantioselective C-H insertion reactions of aryldiazoacetates and α-diazo-β-oxosulfones affording the respective products in up to 93 % ee with excellent trans diastereoselectivity in most cases. Furthermore, efficient desymmetrization in an intramolecular C-H insertion was achieved. In addition, these catalysts prove highly enantioselective for intramolecular aromatic addition with up to 88 % ee, and oxonium ylide formation and rearrangement with up to 74 % ee.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:13 |
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| Enthalten in: |
ChemCatChem - 13(2021), 20 vom: 19. Okt., Seite 4318-4324 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Buckley, Aoife M [VerfasserIn] |
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| Links: |
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| Themen: |
Aromatic Addition |
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| Anmerkungen: |
Date Revised 04.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/cctc.202100924 |
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| 245 | 1 | 0 | |a Dirhodium Carboxylate Catalysts from 2-Fenchyloxy or 2-Menthyloxy Arylacetic Acids |b Enantioselective C-H Insertion, Aromatic Addition and Oxonium Ylide Formation/Rearrangement |
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| 520 | |a © 2021 The Authors. ChemCatChem published by Wiley-VCH GmbH. | ||
| 520 | |a A new class of dirhodium carboxylate catalysts have been designed and synthesized from 2-fenchyloxy or 2-menthyloxy arylacetic acids which display excellent enantioselectivity across a range of transformations of α-diazocarbonyl compounds. The catalysts were successfully applied to enantioselective C-H insertion reactions of aryldiazoacetates and α-diazo-β-oxosulfones affording the respective products in up to 93 % ee with excellent trans diastereoselectivity in most cases. Furthermore, efficient desymmetrization in an intramolecular C-H insertion was achieved. In addition, these catalysts prove highly enantioselective for intramolecular aromatic addition with up to 88 % ee, and oxonium ylide formation and rearrangement with up to 74 % ee | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Aromatic Addition | |
| 650 | 4 | |a Carbenoids | |
| 650 | 4 | |a C−H Insertion | |
| 650 | 4 | |a Diazo Compounds | |
| 650 | 4 | |a Rhodium Catalysis | |
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| 700 | 1 | |a Brouder, Thomas A |e verfasserin |4 aut | |
| 700 | 1 | |a Ford, Alan |e verfasserin |4 aut | |
| 700 | 1 | |a Rao Khandavilli, U B |e verfasserin |4 aut | |
| 700 | 1 | |a Lawrence, Simon E |e verfasserin |4 aut | |
| 700 | 1 | |a Maguire, Anita R |e verfasserin |4 aut | |
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