Efficient pyrimidine N-1-alkylation via activation of electron rich olefins with oxoammonium salts: synthesis of methoxy TEMPO substituted pyrimidine nucleoside analogs.
Our work outlines the use of oxoammonium salts in a formal 1,2 addition process to olefins giving nucleoside analogs as products. Specifically, oxoammonium salts can be added to a solution of olefin and silylated heterocycle to give Methoxy TEMPO substituted nucleoside analogs after hydrolytic workup and chromatographic purification.
Church
Kevin M
KM
Department of Chemistry, University of Dayton, Dayton, Ohio 45469, USA.
Holloway
Liesel M
LM
Matley
Ryan C
RC
Brower
Robert J
RJ
D000475:Alkenes / Q000737:chemistry* / Q000378:metabolism; D000478:Alkylation; D003497:Cyclic N-Oxides / Q000737:chemistry*; D004583:Electrons; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D003497:Cyclic N-Oxides; D011741:Pyrimidine Nucleosides; C062073:4-methoxy-2,2,6,6-tetramethylpiperidinyl-1-oxy