1207362-36-4Relevant articles and documents
Asymmetric radical addition of TEMPO to titanium enolates
Mabe, Phillip J.,Zakarian, Armen
, p. 516 - 519 (2014/04/03)
A mild method for a-hydroxylation of N-acyl oxazolidinones by asymmetric radical addition of the 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO) radical to titanium enolates was developed. The high diastereoselectivity and broad scope of the reaction show synthetic utility for the a-hydroxylation of substrates that are not tolerant to strongly basic conditions.
A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates
Herrmann, Aaron T.,Smith, Lindsay L.,Zakarian, Armen
, p. 6976 - 6979 (2012/06/15)
A Ru-catalyzed direct thermal trifluoromethylation and perfluoroalkylation of N-acyloxazolidinones has been developed. The reaction is experimentally simple and requires inexpensive reagents while providing good yields of products with good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.
Valence tautomerism in titanium enolates: Catalytic radical haloalkylation and application in the total synthesis of neodysidenin
Beaumont, Stephane,Ilardi, Elizabeth A.,Monroe, Lucas R.,Zakarian, Armen
supporting information; experimental part, p. 1482 - 1483 (2010/04/03)
(Chemical Equation Presented) A direct ruthenium-catalyzed radical chloroalkylation of N-acyl oxazolidinones capitalizing on valence tautomerism of titanium enolates has been developed. The chloroalkylation method served as the centerpiece in the enantioselective total synthesis of trichloroleucine-derived marine natural product neodysidenin.