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Stereoselective deconjugation of macrocyclic α,β-unsaturated esters by sequential amidation and olefin transposition: application to enantioselective phase-transfer catalysis.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Homberg, Alexandre Hrdina, Radim Vishe, Mahesh Guénée, Laure Lacour, Jérôme |
| Copyright Year | 2019 |
| Abstract | The stereoselective synthesis of chiral macrocycles bearing two aliphatic amide functional groups is reported. After the amidation mediated by TBD, a guanidine derivative, the olefin transposition step is performed with a slight excess of t-BuOK. The products are afforded in moderate to good combined yields (up to 59%) and with an excellent syn diastereoselectivity (dr > 49 : 1). Introducing enantiopure α-branched substituents was possible and it resulted in mixtures of diastereomers, which could be tested as phase-transfer catalysts using the formation of a phenylalanine analog as a test reaction (up to 43% ee). A clear matched-mismatched situation was observed in the two diastereomeric series. |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c9ob01355e |
| PubMed reference number | 31270519 |
| Journal | Medline |
| Alternate Webpage(s) | https://archive-ouverte.unige.ch/files/downloads/0/0/1/2/0/3/8/5/unige_120385_attachment01.pdf |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/articlepdf/2019/ob/c9ob01355e?page=search |
| Alternate Webpage(s) | https://doi.org/10.1039/c9ob01355e |
| Journal | Organic & biomolecular chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
