Trivalent Phosphine-Catalyzed [4+1] Spiro-annulation Reaction Using Allenyl Imide and Methylene Cyclocompounds
The trivalent phosphine-catalyzed [4+1] spiro-annulation reaction of allenyl imide and activated methylene cyclocompounds has been developed for the construction of various spiro-2-cyclopenten-1-ones. Oxindoles, 3-isochromanones, and 2-indanones are selected as 1C synthons to capture the in situ-generated bis-electrophilic α,β-unsaturated ketenyl phosphonium intermediate, affording the corresponding monospiro- and bispiro-cyclopentenones in good to excellent yields (≤91%) under mild conditions. The primary attempt at asymmetric catalysis using monophosphine (R)-SITCP provides promising enantioselectivity (45% ee). A plausible reaction mechanism is also proposed.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - year:2024 |
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| Enthalten in: |
The Journal of organic chemistry - (2024) vom: 16. Apr. |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhang, Zi-Qiu [VerfasserIn] |
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| Links: |
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Date Revised 16.04.2024 published: Print-Electronic Citation Status Publisher |
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| doi: |
10.1021/acs.joc.4c00388 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM371133289 |
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| 245 | 1 | 0 | |a Trivalent Phosphine-Catalyzed [4+1] Spiro-annulation Reaction Using Allenyl Imide and Methylene Cyclocompounds |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status Publisher | ||
| 520 | |a The trivalent phosphine-catalyzed [4+1] spiro-annulation reaction of allenyl imide and activated methylene cyclocompounds has been developed for the construction of various spiro-2-cyclopenten-1-ones. Oxindoles, 3-isochromanones, and 2-indanones are selected as 1C synthons to capture the in situ-generated bis-electrophilic α,β-unsaturated ketenyl phosphonium intermediate, affording the corresponding monospiro- and bispiro-cyclopentenones in good to excellent yields (≤91%) under mild conditions. The primary attempt at asymmetric catalysis using monophosphine (R)-SITCP provides promising enantioselectivity (45% ee). A plausible reaction mechanism is also proposed | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Zhang, Zhen-Kai |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Yu-Hao |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Bo-Ting |e verfasserin |4 aut | |
| 700 | 1 | |a He, Feng-Kai |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Yi-Long |e verfasserin |4 aut | |
| 700 | 1 | |a Shu, Tao |e verfasserin |4 aut | |
| 700 | 1 | |a Huang, Yi-Yong |e verfasserin |4 aut | |
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