Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions.
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.
Okamoto
Kazuhiro
K
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Hayashi
Tamio
T
Rawal
Viresh H
VH
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D000081005:Cyclohexane Monoterpenes; D008024:Ligands; D039821:Monoterpenes / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D028561:Transition Elements / Q000737:chemistry*
D000475:Alkenes; D000081005:Cyclohexane Monoterpenes; D008024:Ligands; D039821:Monoterpenes; D028561:Transition Elements; C005403:alpha phellandrene
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