Diols are common motifs found in diverse natural products. Here we present the efficient and selective synthesis of 1,4 Diols (4  ) starting from various homoallyl alcohols (1  ). This strategy utilizes Rh(I)-catalyzed one-pot tandem intermolecular dehydrogenative silylation/intramolecular hydrosilylation to regioselectively produce oxasilinane intermediates (3  ), followed by Fleming-Tamao-type oxidation. The initial study revealed that intramolecular 6-endo-cyclization is highly regioselective and catalyst dependent. This tactic will be ultimately applicable to the synthesis of structurally complex and biologically active molecules containing 1,4-diol moieties.

Rhodium-catalyzed regioselective cyclization of homoallyl alcohols via a one-pot tandem dehydrogenative silylation/hydrosilylation: Synthesis of 1,4-diols

245th National Meeting (2013)

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