Work

Asymmetric Total Syntheses of Eliglustat and C2- epi -Eliglustat

Year: 2026

Type: article

Abstract: -eliglustat are reported. Both approaches feature a common key step, which involves a stereocontrolled TMSOTf-mediated aldol-like reaction of azidoacetyl thioimides with dibenzyl acetals of aromatic aldehydes catalyzed by chiral nickel(II) complexes. It is worth noting that the structure of dibenzyl acetals plays a key role in the stereochemical outcome of some of these reactions, as supported by theoretical calculations. Overall, this strategy enables the independent manipulation of the amino and hydroxy functional groups and favors the isolation of enantiomerically pure products.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c03229

Authors: Miguel Mellado-Hidalgo, Anna M. Costa, Pedro Romea, Fèlix Urpí, Gabriel Aullón

Institutions: Institut de Biomedicina de la Universitat de Barcelona, Universitat de Barcelona

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Ministerio de Ciencia, Innovación y Universidades, Generalitat de Catalunya, European Regional Development Fund