Synthesis and absolute configuration of (1 S,8 S)- as-hydrindacene-1,8-diol as determined by the circular dichroism exciton chirality method

[Display omitted] 2,3,6,7-Tetrahydro- as-indacene-1,8-dione 4 was prepared in 4 steps starting from 2-methyl-furan by modification of a literature procedure. Appliance of Noyori’s asymmetric transfer hydrogenation, resulted in (1 S,8 S)-1,2,3,6,7,8-hexahydro- as-indacene-1,8-diol 5 in high yield (81...

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Published inTetrahedron letters Vol. 46; no. 1; pp. 75 - 78
Main Authors Vandyck, Koen, Matthys, Bavo, Van der Eycken, Johan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.01.2005
Elsevier
Subjects
As-hydrindacene-1,8-diol
Chemistry
Chemistry, Organic
Chiral ligands
Circular dichroism
Exciton chirality method
Physical Sciences
Science & Technology
As-hydrindacene-1,8-diol
Chiral ligands
Exciton chirality method
Circular dichroism
as-hydrinclacene-1.8-diol
circular dichroism
exciton chirality method
chiral ligands
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Summary:[Display omitted] 2,3,6,7-Tetrahydro- as-indacene-1,8-dione 4 was prepared in 4 steps starting from 2-methyl-furan by modification of a literature procedure. Appliance of Noyori’s asymmetric transfer hydrogenation, resulted in (1 S,8 S)-1,2,3,6,7,8-hexahydro- as-indacene-1,8-diol 5 in high yield (81%) and excellent enantioselectivity (>99% ee) or (8 S)-8-hydroxy-3,6,7,8-tetrahydro-2 H- as-indacen-1-one 6 in moderate yield (58%) and equally high enantioselectivity (98.5% ee), depending on the conditions. The asymmetric reduction was expected to yield the ( S)-alcohols using the ( S, S)-Ts-DPEN ligand, which was confirmed by the appliance of the exciton chirality method on the corresponding bis( p-dimethylamino)benzoate 7 .
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.11.028