Stannyl phosphaketene as a synthon for phosphorus analogues of β-lactams
The reaction of the stannyl phosphaketene (Nacnac)SnPCO 1 (Nacnac = CH{(CMe)(2,6-iPr2C6H3N)}2) with B(C6F5)3 produced the 1,4-addition product of (Nacnac)SnPCO(B(C6F5)3). However, the corresponding reactions in the presence of dimethyl maleate, diisopropyl fumarate or diethyl-but-2-ynedioate gave [2+2] addition yielding four-membered phosphacycles, ((Nacnac)Sn(MeO2C))CHPC(OB(C6F5)3)CH(CO2Me), [(C6F5)3B)PC(OSn)C(CO2Me)CH(CO2Me)]2, (Nacnac)Sn(iPrO2C)CC(OAl(C6F5)3)P[CH(CO2iPr)CH2(CO2iPr)]CH(CO2iPr), and (Nacnac)SnP (EtO2CCC(CO2Et))CO(B(C6F5)3), respectively. In contrast, the corresponding reaction of phenylacetylene gave the FLP-addition product (Nacnac)SnOC(P)C(Ph)CH(B(C6F5)3). Collectively, this reactivity demonstrates that the stannyl phosphaketene 1 can act as a synthon for P-analogues of β-lactam derivatives.
| Errataetall: |
ErratumIn: Chem Commun (Camb). 2023 Sep 26;59(77):11592. - PMID 37718962 |
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| Medienart: |
E-Artikel |
| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:59 |
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| Enthalten in: |
Chemical communications (Cambridge, England) - 59(2023), 73 vom: 12. Sept., Seite 10956-10959 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Luo, Yong-An [VerfasserIn] |
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| Anmerkungen: |
Date Revised 11.10.2023 published: Electronic ErratumIn: Chem Commun (Camb). 2023 Sep 26;59(77):11592. - PMID 37718962 Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d3cc03117a |
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| funding: |
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| PPN (Katalog-ID): |
NLM361070969 |
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| 500 | |a ErratumIn: Chem Commun (Camb). 2023 Sep 26;59(77):11592. - PMID 37718962 | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The reaction of the stannyl phosphaketene (Nacnac)SnPCO 1 (Nacnac = CH{(CMe)(2,6-iPr2C6H3N)}2) with B(C6F5)3 produced the 1,4-addition product of (Nacnac)SnPCO(B(C6F5)3). However, the corresponding reactions in the presence of dimethyl maleate, diisopropyl fumarate or diethyl-but-2-ynedioate gave [2+2] addition yielding four-membered phosphacycles, ((Nacnac)Sn(MeO2C))CHPC(OB(C6F5)3)CH(CO2Me), [(C6F5)3B)PC(OSn)C(CO2Me)CH(CO2Me)]2, (Nacnac)Sn(iPrO2C)CC(OAl(C6F5)3)P[CH(CO2iPr)CH2(CO2iPr)]CH(CO2iPr), and (Nacnac)SnP (EtO2CCC(CO2Et))CO(B(C6F5)3), respectively. In contrast, the corresponding reaction of phenylacetylene gave the FLP-addition product (Nacnac)SnOC(P)C(Ph)CH(B(C6F5)3). Collectively, this reactivity demonstrates that the stannyl phosphaketene 1 can act as a synthon for P-analogues of β-lactam derivatives | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Zhao, Zhao |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Ting |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Yanguo |e verfasserin |4 aut | |
| 700 | 1 | |a Zhao, Yufen |e verfasserin |4 aut | |
| 700 | 1 | |a Stephan, Douglas W |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Yile |e verfasserin |4 aut | |
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