Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands

Jorge Escorihuela, M. Isabel Burguete, Gregori Ujaque, Agustí Lledós, Santiago V. Luis

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4 Citations (Scopus)

Abstract

© 2016 The Royal Society of Chemistry. 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.
Original languageEnglish
Pages (from-to)11125-11136
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number47
DOIs
Publication statusPublished - 1 Jan 2016

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