948916-65-2Relevant articles and documents
Stereoselective olefination reactions promoted by Rieke manganese
Concellon, Jose M.,Rodriguez-Solla, Humberto,Del Amo, Vicente,Diaz, Pamela
experimental part, p. 2634 - 2645 (2009/12/06)
A study of the advantages of using manganese, an inexpensive and nontoxic metal, to perform stereoselective β-elimination reactions and to promote sequential olefination reactions of aldehydes to obtain α,β- unsaturated esters and amides is presented. Various elimination reactions, all of them characterized by occurring with complete stereoselectivity and in high yields, were performed using active manganese (Mn*) as metalating agent. This ability of manganese has been applied to develop a novel and direct synthesis of (E)-α,β-unsaturated esters or amides and (Z)-α,β-unsaturated α-halo esters and α-choroamides through a Mn*-mediated sequential olefination protocol of aldehydes with dichloro esters or amides and trihalo esters or trichloroamides, respectively. Georg Thieme Verlag Stuttgart.
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.
