Enantioselective silicon-boron additions to cyclic 1,3-dienes catalyzed by the platinum group metal complexes |
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Authors: | Martin Gerdin |
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Affiliation: | KTH School of Chemical Science and Engineering, Organic Chemistry, SE 10044 Stockholm, Sweden |
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Abstract: | 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. |
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Keywords: | Silaboration Interelement Enantioselective Diastereoselective Catalysis |
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