Journal of the American Chemical Society, 2006-06, Vol.128 (25), p.8142-8143
2006
Details
- Autor(en) / Beteiligte
- Titel
- Regiochemical Control in the Metal-Catalyzed Transposition of Allylic Silyl Ethers
- Ist Teil von
- Journal of the American Chemical Society, 2006-06, Vol.128 (25), p.8142-8143
- Ort / Verlag
- Washington, DC: American Chemical Society
- Erscheinungsjahr
- 2006
- Link zum Volltext
- Quelle
- MEDLINE
- Beschreibungen/Notizen
- A novel mode of regiochemical control over the allylic [1,3]-transposition of silyloxy groups catalyzed by Re2O7 has been developed. This strategy relies on a cis-oriented vinyl boronate, generated from the Alder-ene reaction of homoallylic silyl ethers and alkynyl boronates, to trap out the allylic hydroxyl group. The resulting cyclic boronic acids are excellent partners for cross-coupling reactions. High chirality transfer is observed for the rearrangement of enantioenriched allylic silyl ethers.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 0002-7863eISSN: 1520-5126DOI: 10.1021/ja0620639Titel-ID: cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2528283
- Format
- –
- Schlagworte
- Boronic Acids - chemical synthesis, Catalysis, Chemical reactivity, Chemistry, Cyclization, Ethers - chemistry, Exact sciences and technology, Molecular Structure, Organic chemistry, Organosilicon Compounds - chemistry, Propanols - chemistry, Reactivity and mechanisms, Rhenium - chemistry, Ruthenium - chemistry, Stereoisomerism, Vinyl Compounds - chemical synthesis