T. Yakura, A. Ueki, T. Kitamura
Jun 11, 1999
Citations
0
Influential Citations
19
Citations
Journal
Tetrahedron
Abstract
Abstract Methyl (S)-α-diazo-2,2-dimethyl-β-oxo-1,3-dioxolane-2-butanoate (4), upon treatment with dirhodium(II) tetraacetate in refluxing dichloromethane, gave methyl (1S,5S)-2,2-dimethyl-7-oxo-3,8-dioxabicyclo[3.2.1]octane-1-carboxylate (5) via oxonium ylide formation/1,2-shift. On the other hand, a similar treatment of methyl (S)-5,6-bis[tert-butyldimethylsilyl(TBDMS)oxy]-2-diazo-3-oxohexanoate (9a) afforded the C-H insertion product 10 which was directly reduced with lithium aluminum hydride to give stereoselectively (1R,2R,3S,5R)-2,3-bis(TBDMSoxy)-5-hydroxycyclopentanemethanol (13) in 52% yield from 9a.