Enantioselective silicon-boron additions to cyclic 1,3-dienes catalyzed by the platinum group metal complexes
2008 (English)In: Journal of Organometallic Chemistry, ISSN 0022-328X, E-ISSN 1872-8561, Vol. 693, no 23, 3519-3526 p.Article in journal (Refereed) Published
Silaborations of 1,3-cyclohexadiene and 1,3-cycloheptadiene were achieved using catalysts prepared from different combinations of phosphorus ligands and group 10 metal compounds. For the six-membered compound, 1,4-adducts with up to 82% ee were obtained employing Pt(0) and phosphoramidite ligands. For the seven-membered diene optimal conditions were found using catalysts based on Ni(0), but the highest selectivity observed was merely 22% ee. No improvement of the chiral induction was obtained using chiral silylboranes in combination with chiral phosphoramidite ligands in the additions to 1,3-cyclohexadiene. The adduct obtained from cyclohexadiene was used in allylborations of aldehydes under microwave irradiation to produce homoallylic alcohols with moderate to good diastereoselectivity.
Place, publisher, year, edition, pages
Elsevier B. V. , 2008. Vol. 693, no 23, 3519-3526 p.
Silaboration; Interelement; Enantioselective; Diastereoselective; Catalysis
IdentifiersURN: urn:nbn:se:kth:diva-9391DOI: 10.1016/j.jorganchem.2008.08.029ISI: 000259890300008ScopusID: 2-s2.0-53249121378OAI: oai:DiVA.org:kth-9391DiVA: diva2:113837
QC 201007272008-11-032008-10-302010-07-27Bibliographically approved