An Approach to a Chiral Cycloalkanone-Mediated Asymmetric Epoxidation of Stilbene with Oxone^[○!R]
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概要
- 論文の詳細を見る
Chiral and C2-symmetric seven-membered cycloalkanones 2-6 bearing 1, 2-diphenylethane-1, 2-diamine and cyclohexane-1, 2-diamine backbones were synthesized and evaluated their asymmetry inductive behaviours in an asymmetric epoxidation of stilbene with oxone^[○!R]. Although the reaction of the ketones 2 and 3 of a 1, 2-diphenylethane-1, 2-diamine backbone gave stilbene oxide in trace to 31% yield, those of the ketones 4-6 of a cyclohexane-1, 2-diamine backbone gave the epoxide in satisfactorily high yield up to 98%. It is noteworthy that both reactions with use of stoichiometric and substoichiometric amounts of a ketone 4 gave the epoxide in the essentially same enantioselectivity, 17 and 18%. Eleven-membered cyclic ketones 7 and 8 bearing a binaphthalene backbone were also synthesized and examined their behaviours, while the enantioselectivity turned out to be marginal.
- 公益社団法人日本薬学会の論文
- 2001-12-01
著者
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TOMIOKA Kiyoshi
Graduate School of Pharmaceutical Sciences, Kyoto University
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Matsumoto Koichiro
Graduate School Of Pharmaceutical Sciences Kyoto University
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Tomioka Kiyoshi
Graduate School Of Pharmaceutical Sciences Kyoto Univ.
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