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Rh-Catalyzed Synthesis of Benzoxapinones and Benzothiapinones
| Content Provider | Scilit |
|---|---|
| Copyright Year | 2009 |
| Description | Reported is the Rh-catalyzed synthesis of medium-ring heterocycles 2 and 4 via an intramolecular olefin hydroacylation of salicylaldehyde derivatives 1 and 3. Using (R,R)-Me-DuPHOS as the ligand leads preferentially to the 7-membered α-substituted products (>15:1 selectivity). However, 8-membered thioether 5 may be formed selectively in 91% yield using (S,S)-BDDP as ligand. The reaction tolerates electron-rich and electron-deficient substrates with equal efficiency, with excellent yields and enantioselectivities obtained in all cases. The authors also report mechanistic and deuterium-labeling studies, which confirm that heteroatom (O, S) coordination is crucial for the reaction to proceed (no product was observed when S was replaced by $CH_{2}$), and that, in contrast to a previous report, reductive elimination is unlikely to be turnover-limiting (see: M. Brookhart and co-workers J. Am. Chem. Soc. 2007, 129, 2082). |
| Related Links | http://pdfs.semanticscholar.org/1181/43bc2392273ecf202657e61d5f8b108c1ddd.pdf http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0029-1217458.pdf |
| Ending Page | 0839 |
| Page Count | 1 |
| Starting Page | 0839 |
| ISSN | 18611958 |
| e-ISSN | 1861194X |
| DOI | 10.1055/s-0029-1217458 |
| Journal | Synfacts |
| Issue Number | 08 |
| Volume Number | 2009 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2009-07-23 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synfacts Organic Chemistry Em Class Catalyzed Synthesis Electron Rich |
| Content Type | Text |
| Resource Type | Article |
