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Silver-Catalyzed Synthesis of 2,3-Dihydro-pyrroles
| Content Provider | Scilit |
|---|---|
| Author | Strand, D. |
| Editor | Wender, P. A. |
| Copyright Year | 2009 |
| Description | Wender and Strand report the synthesis of 2,3-dihydropyrroles 3 via a formal [3+2] cycloaddition between aziridines 1 and unactivated acetylenes 2 under either Lewis or Brønsted acid catalysis. The silver-catalyzed process is tolerant of a wide range of substrates, including electron-rich and electron-poor acetylenes, and exhibits excellent levels of regioselectivity (>20:1 in favor of C2 $R^{5}$ aryl products). The reaction is not limited to aryl acetylenes, with vinyl and alkyl groups also being tolerated, although $Sc(OTf)_{3}$ was required as catalyst to effect the reaction of the latter substrate. Competition studies showed that electron-rich acetylenes undergo the reaction faster than electron-poor ones, indicating the capture of a cationic intermediate in the product-forming step. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0029-1217780.pdf |
| Ending Page | 0967 |
| Page Count | 1 |
| Starting Page | 0967 |
| ISSN | 18611958 |
| e-ISSN | 1861194X |
| DOI | 10.1055/s-0029-1217780 |
| Journal | Synfacts |
| Issue Number | 09 |
| Volume Number | 2009 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2009-08-21 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synfacts Organic Chemistry Em Class |
| Content Type | Text |
| Resource Type | Article |
