Dynamic Kinetic Asymmetric Hydroacylation: Racemization by Soft Enolization
We report a dynamic kinetic asymmetric transformation (DyKAT) of racemic aldehydes by Rh-catalyzed hydroacylation of acrylamides. This intermolecular hydroacylation generates 1,4-ketoamides with high enantio- and diastereoselectivity. DFT and experimental studies provide mechanistic insights and reveal an unexpected Rh-catalyzed pathway for aldehyde racemization. Our study represents a pioneering kinetic resolution by intermolecular hydroacylation and contributes to the growing field of stereoconvergent catalysis featuring C-C bond construction.
Authors
- Stephanie A. Corio (ORCID: https://orcid.org/0000-0001-9029-3895)
- Jennifer S. Hirschi (ORCID: https://orcid.org/0000-0002-3470-0561)
- Vy M. Dong (ORCID: https://orcid.org/0000-0002-8099-1048)
- Alexander Lu (ORCID: https://orcid.org/0000-0001-7531-9073)
- Erin L. Kuker
- Mengfei Xu (ORCID: https://orcid.org/0000-0002-9486-9887)
- Josephine M. Warnica
Institutions
- Binghamton University (US)
- University of California System (US)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-04-29
- DOI
- https://doi.org/10.1021/jacs.5c01753
- Citations
- 4
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 2.15
Funders
- National Institute of General Medical Sciences
- Division of Chemistry