General Method for the Asymmetric Synthesis of N-H Sulfoximines via C-S Bond Formation
A versatile method for the synthesis of enantioenriched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes molecular oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N-H sulfoximines.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:22 |
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| Enthalten in: |
Organic letters - 22(2020), 7 vom: 03. Apr., Seite 2776-2780 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Mendonça Matos, Priscilla [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 03.04.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.0c00761 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM307644359 |
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a A versatile method for the synthesis of enantioenriched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes molecular oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N-H sulfoximines | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Lewis, William |e verfasserin |4 aut | |
| 700 | 1 | |a Argent, Stephen P |e verfasserin |4 aut | |
| 700 | 1 | |a Moore, Jonathan C |e verfasserin |4 aut | |
| 700 | 1 | |a Stockman, Robert A |e verfasserin |4 aut | |
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