NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
Copyright © 2020, Davies et al.; licensee Beilstein-Institut..
The N-heterocyclic carbene (NHC)-catalyzed formal [2 + 2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring opening with an amine or a reducing agent is described. The resulting β-trifluoromethyl-β-hydroxyamide and alcohol products are produced with reasonable diastereocontrol (typically ≈70:30 dr) and excellent enantioselectivity, and they can be isolated in moderate to good yield as a single diastereoisomer.
Medienart: |
E-Artikel |
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Erscheinungsjahr: |
2020 |
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Erschienen: |
2020 |
Enthalten in: |
Zur Gesamtaufnahme - volume:16 |
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Enthalten in: |
Beilstein journal of organic chemistry - 16(2020) vom: 16., Seite 1572-1578 |
Sprache: |
Englisch |
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Beteiligte Personen: |
Davies, Alyn T [VerfasserIn] |
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Links: |
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Themen: |
Enantioselective catalysis |
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Anmerkungen: |
Date Revised 03.02.2021 published: Electronic-eCollection Citation Status PubMed-not-MEDLINE |
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doi: |
10.3762/bjoc.16.129 |
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funding: |
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Förderinstitution / Projekttitel: |
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PPN (Katalog-ID): |
NLM312803125 |
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520 | |a The N-heterocyclic carbene (NHC)-catalyzed formal [2 + 2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring opening with an amine or a reducing agent is described. The resulting β-trifluoromethyl-β-hydroxyamide and alcohol products are produced with reasonable diastereocontrol (typically ≈70:30 dr) and excellent enantioselectivity, and they can be isolated in moderate to good yield as a single diastereoisomer | ||
650 | 4 | |a Journal Article | |
650 | 4 | |a N-heterocyclic carbene | |
650 | 4 | |a enantioselective catalysis | |
650 | 4 | |a formal [2 + 2] cycloaddition | |
650 | 4 | |a ring opening | |
650 | 4 | |a trifluoromethyl group | |
700 | 1 | |a Greenhalgh, Mark D |e verfasserin |4 aut | |
700 | 1 | |a Slawin, Alexandra M Z |e verfasserin |4 aut | |
700 | 1 | |a Smith, Andrew D |e verfasserin |4 aut | |
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