302571-69-3Relevant academic research and scientific papers
Synthesis of 2,3-dideuterioesters from 2-halo-3-hydroxyesters by using metallic samarium and diiodomethane
Concellón, José M,Huerta, Mónica
, p. 4943 - 4946 (2007/10/03)
2,3-Dideuterioesters are obtained in high yield from 2-chloro-3-hydroxyesters by a sequenced elimination/reduction process promoted by samarium diiodide generated in situ from metallic samarium and diiodomethane.
Sequential elimination-reduction reactions promoted by samarium diiodide: Synthesis of 2,3-dideuterioesters or -amides
Concellon, Jose M.,Rodriguez-Solla, Humberto
, p. 4266 - 4271 (2007/10/03)
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 β-elimination of the starting 2-halo-3-hydroxyesters or -amides 1 and subsequent 1,4-reduction of the obtained α,β-unsaturated esters or amides in the presence of H2O. When D2O is used instead of H2O, 2,3-dideuterioesters or -amides 4 are isolated. A mechanism is proposed to account for this synthesis.
Synthesis of (E)-a,β-unsaturated esters and amides with total selectivity using samarium diiodide
Concellon, Jose M.,Perez-Andres, Juan A.,Rodriguez-Solla, Humberto
, p. 2773 - 2775 (2007/10/03)
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.
