Synthesis of (E)-a,β-unsaturated esters and amides with total selectivity using samarium diiodide

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Abstract

β-elimination of α-halo-β-hydroxyesters 1 was achieved by using samarium diiodide as a metalating reagent, and afforded di- and trisubstituted (E)-α,βunsaturated esters 2 with total steroselectivity. This method has also been extended to the corresponding disubstituted (E)-α,β-unsaturated amides.

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Concellón, J. M., Pérez-Andrés, J. A., & Rodríguez-Solla, H. (2000). Synthesis of (E)-a,β-unsaturated esters and amides with total selectivity using samarium diiodide. Angewandte Chemie - International Edition, 39(15), 2773–2775. https://doi.org/10.1002/1521-3773(20000804)39:15<2773::AID-ANIE2773>3.0.CO;2-W

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