Abstract
Abstract Samarium(II) diiodide-mediated reductive cross-coupling of N -alkylated phthalimides with carbonyl compounds is shown to afford hydroxylated α-hydroxylactams. Ketoamides obtained by dehydration of these compounds through keto-enol tautomer isomerization were reduced with NaBH 4 in a completely stereoselective manner in the presence of CeCl 3 to give threo -aromatic lactams as the sole product. Direct reductive deoxygenation of these α-hydroxylactam intermediates with Et 3 SiH in the presence of Lewis acid also displayed high stereoselectivity to afford the same threo -lactams exclusively. The mechanistic origins of this stereoselectivity are briefly documented.
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