Chemoenzymatic Dynamic Kinetic Resolution of Atropoisomeric 2-(Quinolin-8-yl)benzylalcohols
The chemoenzymatic dynamic kinetic resolution of 2-(quinolin-8-yl)benzylalcohols using a combination of lipases and ruthenium catalysts is described. While CalB lipase performs highly selective enzymatic kinetic resolution, the combination with Shvo's or Bäckvall's catalysts promotes atropisomerization of the substrate via the reversible formation of configurationally labile aldehydes, thereby enabling a dynamic kinetic resolution. This synergistic approach was applied to the synthesis of a variety of heterobiaryl acetates in excellent yields and enantioselectivities.
Authors
- Valentı́n Hornillos (ORCID: https://orcid.org/0000-0002-6181-9146)
- Gonzalo de Gonzalo (ORCID: https://orcid.org/0000-0002-0863-680X)
- Juan M. Coto‐Cid (ORCID: https://orcid.org/0000-0002-7325-1041)
- Rosario Fernández (ORCID: https://orcid.org/0000-0002-1755-1525)
- José M. Lassaletta (ORCID: https://orcid.org/0000-0003-1772-2723)
Institutions
- Instituto de Investigaciones Químicas (ES)
- Universidad de Sevilla (ES)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-09
- DOI
- https://doi.org/10.1021/acs.joc.4c02996
- Citations
- 7
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 6.55
Funders
- Ministerio de Ciencia, Innovación y Universidades
- Junta de Andalucía
- European Regional Development Fund