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Synthesis of 2-Pyrrolidinones by Palladium-Catalyzed [3+2] Cycloaddition of Isocyanates
| Content Provider | Scilit |
|---|---|
| Author | Breinbauer, Rolf Kljajic, Marko Schlatzer, Thomas |
| Copyright Year | 2019 |
| Description | Pd/DPEphos catalyzes the [3+2] cycloaddition of various alkyl isocyanates with 2-acetoxymethyl-3-allyltrimethylsilane as a synthetic equivalent of trimethylenemethane (TMM). Taking advantage of 2-acetoxymethyl-3-allyltrimethylsilane acting both as nucleophile as well as electrophile this reaction gives a convenient access to 5-ring lactams with an exocyclic alkene moiety. The formation of the β,γ-unsaturated 2-pyrrolidinones occurs without olefin isomerization and without epimerization of the stereogenic centers. Mechanistic investigations suggest an initial N-allylation of the isocyanate followed by nucleophilic ring closure furnishing the desired 2-pyrrolidinones. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1610692.pdf |
| Ending Page | 585 |
| Page Count | 5 |
| Starting Page | 581 |
| ISSN | 09365214 |
| e-ISSN | 14372096 |
| DOI | 10.1055/s-0037-1610692 |
| Journal | Synlett |
| Issue Number | 05 |
| Volume Number | 30 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2019-02-19 |
| Access Restriction | Open |
| Subject Keyword | Organic Chemistry Tsuji–trost Allylation |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry |
