Chiral amine/chiral acid as an excellent organocatalytic system for the enantioselective tandem oxa-Michael-aldol reaction
The asymmetric tandem oxa-Michael-aldol reaction of salicylic aldehyde derivatives with alpha,beta-unsaturated aldehydes catalyzed by a chiral amine/chiral acid organocatalytic system was investigated. The organocatalytic system of (S)-diphenylpyrrolinol trimethylsilyl ether with chiral shift reagent (S)-Mosher acid presented a synergistic effect in the improvement of reaction performance and offered an efficient steric effect in the transformation. The tandem oxa-Michael-aldol reaction proceeded with high yields (up to 90%) and with excellent ee values (up to 99%) to give the corresponding chromene derivatives. The structure of the chiral ammonium salt formed in situ and the corresponding mechanism were also studied by (1)H NMR.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2009 |
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| Erschienen: |
2009 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:7 |
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| Enthalten in: |
Organic & biomolecular chemistry - 7(2009), 21 vom: 07. Nov., Seite 4539-46 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Luo, Shu-Ping [VerfasserIn] |
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| Links: |
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| Themen: |
3-hydroxybutanal |
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| Anmerkungen: |
Date Completed 12.01.2010 Date Revised 25.11.2016 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1039/b910835a |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM192068989 |
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| 245 | 1 | 0 | |a Chiral amine/chiral acid as an excellent organocatalytic system for the enantioselective tandem oxa-Michael-aldol reaction |
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| 500 | |a Date Revised 25.11.2016 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a The asymmetric tandem oxa-Michael-aldol reaction of salicylic aldehyde derivatives with alpha,beta-unsaturated aldehydes catalyzed by a chiral amine/chiral acid organocatalytic system was investigated. The organocatalytic system of (S)-diphenylpyrrolinol trimethylsilyl ether with chiral shift reagent (S)-Mosher acid presented a synergistic effect in the improvement of reaction performance and offered an efficient steric effect in the transformation. The tandem oxa-Michael-aldol reaction proceeded with high yields (up to 90%) and with excellent ee values (up to 99%) to give the corresponding chromene derivatives. The structure of the chiral ammonium salt formed in situ and the corresponding mechanism were also studied by (1)H NMR | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Aldehydes |2 NLM | |
| 650 | 7 | |a Amines |2 NLM | |
| 650 | 7 | |a 3-hydroxybutanal |2 NLM | |
| 650 | 7 | |a 8C6G962B53 |2 NLM | |
| 700 | 1 | |a Li, Zhao-Bo |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Li-Ping |e verfasserin |4 aut | |
| 700 | 1 | |a Guo, Yi |e verfasserin |4 aut | |
| 700 | 1 | |a Xia, Ai-Bao |e verfasserin |4 aut | |
| 700 | 1 | |a Xu, Dan-Qian |e verfasserin |4 aut | |
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