Open Accessα-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines
Author(s) -
Kristen M. Baker,
Amanda Tallon,
Richard P. Loach,
Olivia P. Bercher,
Matthew A. Perry,
Mary P. Watson
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c02708
Subject(s) - chemistry , enantiopure drug , deamination , stereocenter , organic chemistry , potassium carbonate , combinatorial chemistry , catalysis , enantioselective synthesis , enzyme
A deaminative reaction of Katritzky alkylpyridinium salts and sulfinimines has been developed to deliver enantiopure α-chiral amines. The success of this method relied on the discovery of a thermally promoted deamination via single-electron transfer of an anion-π complex of the alkylpyridinium cation with potassium carbonate. This method boasts excellent diastereoselectivity over the α-stereocenter as well as broad functional group and heterocycle tolerance.