Exploitation of Highly Stereoseletive Iodolactamization Using Thioamide Group

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<gamma>,<delta>-Unsaturated thioimidates underwent regio-, stereo-, and diastereoselective iodine-induced lctamization to afford functionalized <gamma>-lactams, which were transformed into biologically active compuds [formal total synthesis of (-)-detoxinine, (<+->-trans-2-hydroxymethyl-3-hydroxy-pyrrolidine isolated from Castanospermum australe, <delta>-coniceine, the key intermediate of (<+->)-slaframine, and the constituent of fosenopril (angiotensin converting enzyme inhibitor)].Iodolactamization of <delta>,<epsilon>-unsaturated thioimidates proceeded regioselectively to provide <delta>-lactams. In this study, we found a new homoenolate reagent (<beta>-tributylstanylpropion-secondary-amide).