Koen Vandyck, B. Matthys, J. V. D. Eycken
Jan 3, 2005
Citations
0
Influential Citations
9
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 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 .