Asymmetric Desymmetrization of Saturated and Unsaturated meso-1,2-Diols

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 i...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 52; pp. 10141 - 10151
Main Authors Fujioka, Hiromichi, Nagatomi, Yasushi, Kotoku, Naoyuki, Kitagawa, Hidetoshi, Kita, Yasuyuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.12.2000
Elsevier
Subjects
asymmetric desymmetrization
Chemistry
Chemistry, Organic
ene acetal
intramolecular haloetherification
meso-1,2-diol
norbornene aldehyde
Physical Sciences
Science & Technology
ene acetal
asymmetric desymmetrization
meso-1,2-diol
intramolecular haloetherification
norbornene aldehyde
L-MENTHONE
ACYLATION
ENE ACETALS
DIASTEREOSELECTIVE BETA-ELIMINATION
INDUCTION
ACTIVE COMPOUNDS
CHIRAL ALPHA
MESO-DIOLS
ALPHA-ARYLSULFINYL ACETALS
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Summary: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.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00859-0