Masithi, Phathutshedzo, Bhana, Ashlyn D., Venter, Gerhard A. et al. (4 more authors) (2024) Cinchona Organocatalyzed Enantioselective Amination for Quaternized Serines as Tertiary Amides. Organic letters. 9162–9167. ISSN 1523-7052
Abstract
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 DtBAD, which occurs from the Re face of an H-bonded enaminone when using a 9S-cinchonamine catalyst, resulting in a hydrazide with the R-configuration as determined by X-ray analysis.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | Publisher Copyright: © 2024 The Authors. Published by American Chemical Society. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number WELLCOME TRUST 225257/Z/22/Z |
Depositing User: | Pure (York) |
Date Deposited: | 08 Nov 2024 10:30 |
Last Modified: | 21 Jan 2025 18:15 |
Published Version: | https://doi.org/10.1021/acs.orglett.4c03650 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1021/acs.orglett.4c03650 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:219373 |
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Description: Cinchona Organocatalyzed Enantioselective Amination forQuaternized Serines as Tertiary Amides
Licence: CC-BY 2.5