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Enantioselective Darzens reaction using organoselenide-lithium hydroxide complexes |
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| Authors: | Shin-ichi Watanabe Risa Hasebe Hideko Nagasawa |
| Institution: | a College of Pharmacy, Kinjo Gakuin University, 1723 Omori 2 chome, Moriyama-ku, Nagoya 463-8521, Japan b Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan c Yokohama College of Pharmacy, 601 Matanocho, Totsuka-ku, Yokohama 245-0066, Japan |
| Abstract: | Asymmetric Darzens reaction catalyzed by chiral selenides is described. A novel Lewis acid/Brønsted base catalyst formed by C2 symmetric chiral selenide-bearing isoborneol skeletons, which were readily prepared from (1S)-10-camphorsulfonic acid, and LiOH promoted the reaction of phenacyl bromide with aldehydes to afford the desired trans oxiranes with up to 62% ee. |
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