Silaborative Carbocyclization of 1,6-Enynes
(English)Manuscript (Other academic)
The silaboration of 1,6-enynes gives densely functionalized five-membered rings that offer promising reactivities for further synthetic manipulations. We have found that using silylborane 4 silaborative carbocyclization reactions proceed in good to excellent yields, giving the product as a single diastereomer. Attempts to extend this methodology to include terminally substituted enynes and developing asymmetric versions were largely unsuccessful. The vinylboronates formed were employed in Suzuki cross-coupling reactions with a range of aryl bromides, furnishing arylated product in good yields.
IdentifiersURN: urn:nbn:se:kth:diva-9394OAI: oai:DiVA.org:kth-9394DiVA: diva2:113840
QC 201009242008-11-032008-10-302010-09-24Bibliographically approved