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Sequential elimination-reduction reactions promoted by samarium diiodide: synthesis of 2,3-dideuterioesters or
J M Concellón1, H Rodríguez-Solla
1Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Spain. jmcg@sauron.quimica.uniovi.es
Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 1, 2001
Abstract:
A facile and general sequential elimination/reduction process promoted by samarium diiodide provides an efficient method for synthesizing saturated esters or amides 3 from readily available starting materials. The reaction involves a beta-elimination of the starting 2-halo-3-hydroxyesters or -amides 1 and subsequent 1,4-reduction of the obtained alpha,beta-unsaturated esters or amides in the presence of H2O. When D20 is used instead of H2O, 2,3-dideuterioesters or -amides 4 are isolated. A mechanism is proposed to account for this synthesis.