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3-Bromopropenyl Methyl Carbonate: A New Reagent for the α-Hydroxy Allylation Reaction of Aldehydes in Water
| Content Provider | Scilit |
|---|---|
| Author | Lombardo, Marco Trombini, Claudio Pasi, Filippo Tiberi, Caterina |
| Copyright Year | 2005 |
| Description | 3-Bromopropenyl methyl carbonate reacts smoothly with aldehydes in the presence of zinc in a mixture of saturated aqueous $NH_{4}$Cl and THF (9:1). Monoprotected alk-1-en-3,4-diols are formed in high yields and in short reaction times. The reaction is diastereoselective, saturated aldehydes afford anti-adducts, while α,β-unsaturated and aromatic aldehydes preferentially give the syn-isomers. Very simple conditions for the conversion of intermediate monocarbonate derivatives of alk-1-en-3,4-diols to cyclic carbonates are also reported. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2005-872144.pdf |
| Ending Page | 2614 |
| Page Count | 6 |
| Starting Page | 2609 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-2005-872144 |
| Journal | Synthesis |
| Issue Number | 15 |
| Volume Number | 2005 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2005-08-04 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry 3-bromopropenyl Carbonates Heterosubstituted Allyl Zinc Complexes Monoprotected Alk-1-en-3 |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
