199122-70-8Relevant articles and documents
Asymmetric desymmetrization of saturated and unsaturated meso-1,2-diols
Fujioka, Hiromichi,Nagatomi, Yasushi,Kotoku, Naoyuki,Kitagawa, Hidetoshi,Kita, Yasuyuki
, p. 10141 - 10151 (2007/10/03)
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. (C) 2000 Elsevier Science Ltd.