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Copper-Catalyzed Ring-Opening of Heterobicyclic Alkenes with Grignard Reagents: Remarkably Highanti-Stereocontrol
| Content Provider | Scilit |
|---|---|
| Author | Arrayás, Ramón Gómez Carretero, Juan Carlos Cabrera, Silvia |
| Copyright Year | 2006 |
| Description | Unlike most of the reported protocols for the ring-opening reaction of heterobicyclic alkenes with carbon nucleophiles which typically occur with syn selectivity, the alkylative ring-opening reaction of [2.2.1]oxa- and azabicyclic alkenes with Grignard reagents in the presence of a catalytic amount of copper(I) takes place with very high or complete anti-stereocontrol under smooth reaction conditions. This new procedure proved to be wide in scope with respect to both the Grignard reagent and the bicyclic alkene. Especially noteworthy is the facile ring-opening reaction of low reactive substrates such as nonaromatic oxabicyclic alkenes and azabenzonorbornadienes under this catalyst system. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-926379.pdf |
| Ending Page | 1219 |
| Page Count | 15 |
| Starting Page | 1205 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-2006-926379 |
| Journal | Synthesis |
| Issue Number | 7 |
| Volume Number | 2006 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2006-03-08 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Ring-opening Reaction Oxabicyclic Alkenes Azabenzonorbornadiene Grignard Reagents (2-pyridyl)sulfonamides |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
