Vanadium(V)-Catalyzed Oxidative Bromination of Acid Labile Alkenols and Alkenes in Alkyl Carbonates
Bruecher, O; Hartung, J
| HERO ID | 4305183 |
|---|---|
| In Press | No |
| Year | 2011 |
| Title | Vanadium(V)-Catalyzed Oxidative Bromination of Acid Labile Alkenols and Alkenes in Alkyl Carbonates |
| Authors | Bruecher, O; Hartung, J |
| Volume | 1 |
| Issue | 11 |
| Page Numbers | 1448-1454 |
| Abstract | Molecular bromine is formed from bromide and tert-butyl hydroperoxide under mild and neutral conditions. The oxidation is catalyzed by vanadium(V)-complexes and requires bromide- and proton- aliquots that are slowly released from a 3-bromopropionic acid-bromide buffer in solutions of alkyl carbonates. In such an environment, bromocyclization of acid labile alkenols occurs without hydrolytically cleaving acetal- or ester-protecting groups. 4-Pentenols having methyl- and/or phenyl-groups attached to the terminal carbon atom of the alkenol double bond undergo 6-endo-selective ring closures if subjected to oxidative bromination and provide bromotetrahydropyrans in synthetically useful yields. Application of the new procedure affords a hexasubstituted tetrahydropyran-building block en route to synthesis of the marine natural product aplysiapyranoid A. |
| Doi | 10.1021/cs200349c |
| Wosid | WOS:000296598000001 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Journal:ACS CATALYSIS 2155-5435 |
| Is Public | Yes |
| Keyword | alkyl carbonate; alkyl hydroperoxide; bromocyclization; bromoperoxidase model; oxidation catalysis; vanadium(V) complex |