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    Diastereoselective Synthesis of Pentasubstituted γ-Butyrolactones from Silyl Glyoxylates and Ketones through a Double Reformatsky Reaction

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    Three contiguous stereocenters can be established with remarkable diastereoselectivity in a double Reformatsky sequence. Densely functionalized gamma-butyrolactones were assembled rapidly by this approach, in which a ketone is used as the terminal electrophile (see scheme). Secondary transformations of the lactone products enhance their synthetic utility. R(1) = Me, H; R(2) = alkyl, aryl, CF(3); Bn = benzyl, TBS = tert-butyldimethylsilyl
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