Asymmetric Desymmetrization of Saturated and Unsaturated meso-1,2-Diols |
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Authors: | Hiromichi Fujioka Yasushi Nagatomi Naoyuki Kotoku Hidetoshi Kitagawa Yasuyuki Kita |
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Institution: | Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan |
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Abstract: | An asymmetric desymmetrization of saturated and unsaturated cyclic and acyclic meso-1,2-diols has been developed from the ene acetals, prepared from the norbornene carboxyaldehyde and meso-1,2-diols. The intramolecular haloetherification of the ene acetals as a key step afforded 8-membered acetals in a stereoselective manner just by the reaction of norbornene olefin even when the ene acetals from unsaturated meso-1,2-diols having olefins in the same molecule were used. Subsequent reductive elimination, followed by protecting the hydroxy group and transacetalization, gave optically active 1,2-diol derivatives and the starting ene acetals in good yields. |
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Keywords: | asymmetric desymmetrization meso-1 2-diol norbornene aldehyde intramolecular haloetherification ene acetal |
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