Fig. 3: Scope of the Fe-catalysed hydroamidation of complex alkenes including natural products.

Conditions: alkene (0.2 mmol) in EtOH–DCM (1:1, 2 ml). Fe(dibm)₃ (10 mmol%): iron tris(diisobutyrylmethane). Phenylsilane (0.6 mmol). Reagent 2o (0.24 mmol). n.f., no functionalization; Bpin, pinacolborane. X-ray structure of compounds 3y, 3ag, 3ah and 3ai. Reactions were carried out on 0.1 mmol scale, and all yields provided refer to isolated yields. Diastereoselectivity (if applicable) was determined by gas chromatography or NMR spectroscopy analysis, and the relative configuration was assigned by X-ray analysis of single crystals or in analogy to a known related compound. r.r., regioselectivity ratio; Cbz, benzyloxycarbonyl. ^aMajor isomer of the two inseparable regioisomers drawn. ^bRegioisomers could not be unambiguously assigned. In products 3p, 3q, 3r, 3ab and 3ac, the two black dots indicate the sites where the N atom is attached to the carbon backbone in the two regioisomers. However, only one regioisomer is depicted in the figure.