Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with a-amino amide ligands
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Altres documents de l'autoria: Escorihuela, Jorge; Burguete, M. Isabel; Ujaque, Gregori; Lledós, Agustí; Luis, Santiago V.
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Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with a-amino amide ligandsData de publicació
2016-11Editor
The Royal Society of ChemistryCita bibliogràfica
ESCORIHUELA, Jorge, et al. Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands. Organic & Biomolecular Chemistry, 2016, vol. 14, no 47, p. 11125-11136.Tipus de document
info:eu-repo/semantics/articleVersió de l'editorial
http://pubs.rsc.org/en/content/articlehtml/2016/ob/c6ob01878eParaules clau / Matèries
Resum
The enantioselective alkylation of aldehydes catalysed by nickel(II)-complexes derived from α-amino amides was studied by means of density functional theory (DFT) and ONIOM (B3LYP:UFF) calculations. A mechanism was ... [+]
The enantioselective alkylation of aldehydes catalysed by nickel(II)-complexes derived from α-amino amides was studied by means of density functional theory (DFT) and ONIOM (B3LYP:UFF) calculations. A mechanism was proposed in order to investigate the origin of enantioselectivity. The chirality-determining step for the alkylation was the formation of the intermediate complexes with the involvement of a 5/4/4-fused tricyclic transition state. The predominant products predicted theoretically were of (S)-configuration, in good agreement with experimental observations. The scope of the reaction was examined and high yields and enantioselectivities were observed for the enantioselective addition of Et2Zn and Me2Zn to aromatic and aliphatic aldehydes. [-]
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Org. Biomol. Chem., 2016, 14Drets d'accés
© The Royal Society of Chemistry 2016
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