Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions |
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Authors: | Okamoto Kazuhiro Hayashi Tamio Rawal Viresh H |
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Affiliation: | Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. |
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Abstract: | Chiral dienes possessing the bicyclo[2.2.2]octadiene framework were prepared readily through the [4 + 2] cycloaddition of ( R)-alpha-phellandrene with methyl propiolate as the key step. Diene 9, substituted with a tertiary alcohol on one of the two double bonds, is prepared in just one step from the cycloadduct and is highly effective as a chiral ligand for rhodium-catalyzed asymmetric conjugate addition reactions, giving the corresponding addition products with higher enantioselectivity than other chiral dienes. |
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