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Problem Set 2-solution

Problem Set 2-solution - Chem 3580 Spring 2010 1...

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Chem 3580 - Spring 2010 Problem Set #2 – solutions 1. Retrosynthesis Br Br Gilman + CuLi 2 Retroynthesis for the Gilman reagent CuLi 2 Br CuLi 2 Br + Proposed forward synthesis Br 2 FeBr 3 Br CuLi 2 NBS Peroxide Br Gilman reagent Br CuLi 2 1. BH 3 2. H 2 O 2 , HO 3. PBr 3 Br CuLi 2 1. Li 2. CuI ———————————————————————————————————————————— Retrosynthesis H O H OH MgBr + O Forward synthesis Br THF (solvent) MgBr O H OH MnO 2 , ! (Chem 3580) H O or PCC (Chem 3570) (Chem 3570) (Chem 3570) Mg ———————————————————————————————————————————— Retrosynthesis OH Br Hydration Gilman Cl AlCl 3 NBS, peroxide Br OH t-BuOK H 2 O H 2 SO 4 (cat) Alternate route using Gilman coupling. Note how much this retduced the number of steps. OH H 2 O H 2 SO 4 (cat) CuLi 2
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2. Cl O Cl O SnCl 4 C O ClSnCl 4 + SnCl 4 + O C O O H O H O H O O O O O B ————————————————————————————————————————————
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