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Cinchona Organocatalyzed Enantioselective Amination for Quaternized Serines as Tertiary Amides

Year: 2024
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Herein, we describe a Cinchona -aminocatalyzed enantioselective α-hydrazination of an α-formyl amide for the production of protected quaternized serines as tertiary amides with ee ’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 t BAD, which occurs from the Re face of an H-bonded enaminone when using a 9 S -cinchonamine catalyst, resulting in a hydrazide with the R -configuration as determined by X-ray analysis.
DOI: 10.1021/acs.orglett.4c03650
Authors: Phathutshedzo Masithi, Ashlyn D. Bhana, Gerhard A. Venter, Hong Su, Christopher D. Spicer, Wade F. Petersen, Roger Hunter
Language: English
Field: Chemistry
Open Access status: hybrid
Estimated APC paid: $4,500
Funders: Wellcome Trust, Royal Society, Research Councils UK, Royal Society of Chemistry, National Research Foundation, University of Cape Town, Center for High Performance Computing, Engineering and Physical Sciences Research Council
OpenAlex ID: W4403454616
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Cites: 67
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Related to: 10