302571-80-8

Upstream product

• 302571-78-4 2-Chloro-N,N-diethyl-3-hydroxy-4-phenylpentanamide 
• 921-88-0 N,N-diethyldichloroacetamide 
• 34713-70-7 2-Phenylpropanal 
• 1211382-30-7 rac-(E)-N,N-diethyl-4-[(methanesulfonyl)oxy]-2-pentenamide 
• 100-58-3 phenylmagnesium bromide 
• 2315-36-8 2-Chloro-N,N-diethylacetamide 

Relevant academic research and scientific papers

Iron-Catalyzed Regio- And Stereoselective Substitution of γ,δ-Epoxy-α,β-unsaturated Esters and Amides with Grignard Reagents

Chemical Equetion Presentation When γ,δ-epoxy-α,β- unsaturated esters or amides were treated with 2 equiv of Grignard reagents in the presence of 10-24 mol % FeCl2, regio- and stereoselective substitution of the epoxide moiety with the Grignard reagent occurred to give exclusively δ-hydroxy-γ-alkyl or aryl-α,β-unsaturated esters or amides in good yields.

Stereoselective olefination reactions promoted by Rieke manganese

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

(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.

Very rapid preparation of SmI2 by sonic treatment of iodoform and metallic samarium

A very rapid preparation of SmI2 by sonication of a mixture of metallic samarium and iodoform in THF is described. To prove the synthetic applications of the obtained SmI2 several high-yielding reactions were carried out. Preliminary results for the generation of SmI2 in THF by sonication from diiodomethane, 1,2-diiodoethane, or iodine are also described. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Synthesis of (E)-α,β-unsaturated amides with high selectivity by using samarium diiodide

Stereoselective β-elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield α,β-unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds 1 are easily prepared by reaction of the c

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 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

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.