<i>Cinchona</i> Organocatalyzed Enantioselective Amination for Quaternized Serines as Tertiary Amides
Herein, we describe a <i>Cinchona</i>-aminocatalyzed enantioselective α-hydrazination of an α-formyl amide for the production of protected quaternized serines as tertiary amides with <i>ee</i>'s of generally >98% and ≤99% yields. The proposed TS model supported by density functional theory calculations involves a quinuclidinium ion Brønsted acid-assisted delivery of D<sup><i>t</i></sup>BAD, which occurs from the <i>Re</i> face of an H-bonded enaminone when using a 9<i>S</i>-cinchonamine catalyst, resulting in a hydrazide with the <i>R</i>-configuration as determined by X-ray analysis.
Authors
- Wade F. Petersen (ORCID: https://orcid.org/0000-0003-3215-5560)
- Gerhard A. Venter (ORCID: https://orcid.org/0000-0003-3993-1198)
- Christopher D. Spicer (ORCID: https://orcid.org/0000-0001-8787-578X)
- Roger Hunter
- Ashlyn D. Bhana
- Hong Su (ORCID: https://orcid.org/0000-0002-7663-8911)
- Phathutshedzo Masithi (ORCID: https://orcid.org/0000-0001-8222-9789)
Institutions
- University of Cape Town (ZA)
- University of York (GB)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-16
- DOI
- https://doi.org/10.1021/acs.orglett.4c03650
- Primary Topic
- Advanced Synthetic Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Wellcome Trust
- Royal Society
- Royal Society of Chemistry
- National Research Foundation
- University of Cape Town
- Center for High Performance Computing
- Engineering and Physical Sciences Research Council