Academic Journal
One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening
| العنوان: | One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening |
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| المؤلفون: | Alastair J. Nimmo, Kevin Kasten, George White, Julia Roeterdink, Aidan P. McKay, David B. Cordes, Andrew David Smith |
| المصدر: | Molecules, Vol 29, Iss 15, p 3635 (2024) |
| بيانات النشر: | MDPI AG |
| سنة النشر: | 2024 |
| المجموعة: | Directory of Open Access Journals: DOAJ Articles |
| مصطلحات موضوعية: | malamides, organocatalysis, isothiourea, β-lactone ring-opening, oxindole ring-opening, asymmetric synthesis, Organic chemistry, QD241-441 |
| الوصف: | Malamides (diamide derivatives of malic acid) are prevalent in nature and of significant biological interest, yet only limited synthetic methods to access functionalised enantiopure derivatives have been established to date. Herein, an effective synthetic method to generate this molecular class is developed through in situ formation of spirocyclic β-lactone-oxindoles (employing a known enantioselective isothiourea-catalysed formal [2+2] cycloaddition of C(1)-ammonium enolates and isatin derivatives) followed by a subsequent dual ring-opening protocol (of the β-lactone and oxindole) with amine nucleophiles. The application of this protocol is demonstrated across twelve examples to give densely functionalised malamide derivatives with high enantio- and diastereo-selectivity (up to >95:5 dr and >99:1 er). |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| تدمد: | 1420-3049 |
| Relation: | https://www.mdpi.com/1420-3049/29/15/3635; https://doaj.org/toc/1420-3049; https://doaj.org/article/6104594db1a14f3e8c72f4c02089e166 |
| DOI: | 10.3390/molecules29153635 |
| الاتاحة: | https://doi.org/10.3390/molecules29153635 https://doaj.org/article/6104594db1a14f3e8c72f4c02089e166 |
| رقم الانضمام: | edsbas.BFEC930A |
| قاعدة البيانات: | BASE |
Full Text Finder | تدمد: | 14203049 |
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| DOI: | 10.3390/molecules29153635 |