Sequential elimination-reduction reactions promoted by samarium diiodide: synthesis of 2,3-dideuterioesters or -amides.
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.
Concellón
J M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Spain. jmcg@sauron.quimica.uniovi.es
Rodríguez-Solla
H
H
D000577:Amides / Q000138:chemical synthesis*; D003903:Deuterium / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis*; D007454:Iodides / Q000737:chemistry*; D007553:Isotope Labeling / Q000379:methods*; D012493:Samarium / Q000737:chemistry*
D000577:Amides; D004952:Esters; D007454:Iodides; D012493:Samarium; D003903:Deuterium; C409809:samarium diiodide