Highly diastereoselective entry to chiral oxindole-based β-amino boronic acids and spiro derivatives
| العنوان: | Highly diastereoselective entry to chiral oxindole-based β-amino boronic acids and spiro derivatives |
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| المؤلفون: | Stefano Gazzotti, Leonardo Lo Presti, Alessandra Silvani, Marco Manenti, Giorgio Molteni |
| المصدر: | Organic & Biomolecular Chemistry. 19:7211-7216 |
| بيانات النشر: | Royal Society of Chemistry (RSC), 2021. |
| سنة النشر: | 2021 |
| مصطلحات موضوعية: | Steric effects, chemistry.chemical_compound, chemistry, Peptidomimetic, Organic Chemistry, Diastereomer, Oxindole, Physical and Theoretical Chemistry, Biochemistry, Combinatorial chemistry, Stereocenter |
| الوصف: | We here describe the first Cu-catalysed, diastereoselective 1,2-addition of 1,1-diborylmethane to chiral ketimines for the synthesis of quaternary stereocenters and spiro compounds. The method provides easy access to a range of chiral, highly functionalized compounds, namely oxindole-based β,β'-disubstituted β-amino boronates, boron-containing peptidomimetics and six-, seven-membered spirocyclic hemiboronic esters. Such unprecedented compounds are mostly obtained in high yields and easily isolated as single diastereoisomers, paving the way to a more intense exploitation of boron-containing compounds in diversity-oriented chemistry and drug-discovery programs. Concerning stereochemistry, the application of Ellman's auxiliary strategy allows in principle to access both steric series of target compounds. |
| تدمد: | 1477-0539 1477-0520 |
| DOI: | 10.1039/d1ob01303c |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e92ed06d023d3bc5bd21b62ccef595a6 https://doi.org/10.1039/d1ob01303c |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi.dedup.....e92ed06d023d3bc5bd21b62ccef595a6 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 14770539 14770520 |
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| DOI: | 10.1039/d1ob01303c |