Li, Chengxi published the artcileEngaging aldehydes in CuH-catalyzed reductive coupling reactions: stereoselective allylation from 1,3-diene pronucleophiles, Computed Properties of 1468-83-3, the main research area is copper hydride catalyst stereoselective allylation aldehyde diene mol modeling; aldehydes; allylic compounds; copper; dienes; reductive coupling.
Recently, CuH-catalyzed reductive coupling processes involving carbonyl compounds and imines have become attractive alternatives to traditional methods for stereoselective addition because of their ability to use readily accessible and stable olefins as surrogates for organometallic nucleophiles. However, the inability to use aldehydes, which usually reduce too rapidly in the presence of copper hydride complexes to be viable substrates, has been a major limitation. Shown here is that by exploiting relative concentration effects through kinetic control, this intrinsic reactivity can be inverted and the reductive coupling of 1,3-dienes with aldehydes achieved. Using this method, both aromatic and aliphatic aldehydes can be transformed into synthetically valuable homoallylic alcs. with high levels of diastereo- and enantioselectivities, and in the presence of many useful functional groups. Furthermore, using a combination of theor. (DFT) and exptl. methods, important mechanistic features of this reaction related to stereo- and chemoselectivities were uncovered. Recently, CuH-catalyzed reductive coupling processes involving carbonyl compounds and imines has become an attractive alternative to traditional methods for stereoselective addition to carbonyls due to the ability to use readily accessible and stable olefin-derived pronucleophiles as surrogates for organometallic reagents. However, the inability to use aldehydes, which traditionally reduce too rapidly in the presence of copper hydride complexes to be viable substrates, has been a major limitation. We show that by exploiting relative concentration effects through slow addition, we can invert this intrinsic reactivity and achieve the reductive coupling of 1,3-dienes with aldehydes. Using this method, both aromatic and aliphatic aldehydes can be transformed to valuable products with high levels of diastereo- and enantioselectivity and in the presence of many useful functional groups. Furthermore, using a combination of theor. (DFT) and exptl. methods, important mechanistic features of this reaction related to stereo- and chemoselectivity were uncovered.
Angewandte Chemie, International Edition published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Computed Properties of 1468-83-3.
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem