K. Tamao, E. Nakajo, Y. Ito*
1988
Citations
0
Influential Citations
35
Citations
Journal
Tetrahedron
Abstract
Abstract An organocopper reagent, derived from allyl(diethylamino)dimethylsilane via metalation by n-BuLi/TMEDA followed by transmetalation, reacts with aldehydes regioselectively at the γ position to form 1-substituted ( E )-3-buten-1-ol derivatives. Epoxidation of the double bond followed by hydrogen peroxide cleavage of the carbonsilicon bond affords 2,3-dihydroxy-tetrahydrofuran derivatives, which are further transformed into 2-deoxy-C-nucleoside skeletons via siloxymethylation at the anomeric position. One model system is presented, together with the stereochemical aspects.