Silafunctional compounds in organic synthesis. 40.1 metalated (allyl) aminosilanes: a γ-regioselective reaction with aldehydes and an approach to the synthesis of 2-deoxy-c-nucleoside skeletons

Add time:08/06/2019    Source:sciencedirect.com

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.

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