Cinchona Organocatalyzed Enantioselective Amination for Quaternized Serines as Tertiary Amides

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 involve...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 26; no. 42; pp. 9162 - 9167
Main Authors Masithi, Phathutshedzo, Bhana, Ashlyn D., Venter, Gerhard A., Su, Hong, Spicer, Christopher D., Petersen, Wade F., Hunter, Roger
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 25.10.2024
Subjects
Letter
Online AccessGet full text

Cover

More Information
Summary: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 9S-cinchonamine catalyst, resulting in a hydrazide with the R-configuration as determined by X-ray analysis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03650