288093-79-8Relevant academic research and scientific papers
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 reactions promoted by manganese: Completely stereoselective synthesis of (E)-α,β-unsaturated amides, ketones, aldehydes, and carboxylic acids
Concellon, Jose M.,Rodriguez-Solla, Humberto,Diaz, Pamela
, p. 7974 - 7979 (2008/02/13)
(Chemical Equation Presented) A complete E-selective synthesis of α,β-unsaturated amides through a sequential reaction of a range of dichloroamides with a variety of aldehydes promoted by Rieke manganese (Mn*) is reported. A mechanism based on a sequential aldol-type reaction and a completely stereoselective β-elimination is proposed to explain these results. The unsaturated amides obtained are readily and efficiently transformed into α,β-unsaturated ketones, aldehydes, or carboxylic acids without loss of the diastereoisomeric purity of the C-C double bond.
