ChemInform Abstract: Novel and Stereoselective Methods for the Preparation of Aromatic Lactams via Reductive Coupling Reactions Mediated by SmI2.
Abstract
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ChemInform Abstract
The first example of samarium(II) diiodide mediated coupling reaction of aromatic N-alkylimides (I) with carbonyl compounds (II) is described. The reduction of the corresponding ketoamides (IV), derived from dehydration of the coupling products, with NaBH4 in the presence of CeCl3 occurs with high stereoselectivity, leading to threo-aromatic lactams (V). Furthermore, direct reductive deoxygenation of (III) with Et3SiH in the presence of Lewis acid also affords the same threo-lactams (V) with high stereoselectivity.
