1246927-41-2Relevant academic research and scientific papers
Iridium-Catalyzed Enantioselective Allylic Substitutions of Racemic, Branched Trichloroacetimidates with Heteroatom Nucleophiles: Formation of Allylic C?O, C?N, and C?S Bonds
Arachchi, Madhawee K.,Nguyen, Hien M.
supporting information, p. 4239 - 4246 (2021/07/16)
A broadly applicable methodology for the regio- and enantioselective construction of branched allylic carbon-heteroatom bonds from racemic, secondary allylic trichloroacetimidates has been developed. The branched allylic substrates undergo dynamic kinetic asymmetric substitution reactions with a number of unactivated anilines and carboxylic acids as well as unactivated aromatic thiols in the presence of a chiral bicyclo[3.3.0]octadiene-ligated iridium catalyst. The allylic C?O, C?N, and C?S bond containing products are obtained in synthetically useful yield and selectivity. Mechanistic studies suggest that the iridium-catalyzed enantioselective substitution reactions of heteroatom nucleophiles with allylic trichloroacetimidate substrates through an outer-sphere nucleophilic addition mechanism. In addition, the chiral diene-ligated iridium catalyst is effective at promoting asymmetric aminations of acyclic secondary anilines. Importantly, this catalytic iridium methodology enables the use of alkyl substituted allylic electrophiles. (Figure presented.).
Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines
Arnold, Jeffrey S.,Cizio, Gregory T.,Heitz, Drew R.,Nguyen, Hien M.
supporting information, p. 11531 - 11533,3 (2012/12/12)
We report the chiral diene ligated rhodium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of racemic secondary allylic trichloroacetimidates with a variety of N-methyl anilines, providing allylic N-methyl arylamines in high yields, regioselec
Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines
Arnold, Jeffrey S.,Cizio, Gregory T.,Heitz, Drew R.,Nguyen, Hien M.
supporting information, p. 11531 - 11533 (2013/01/15)
We report the chiral diene ligated rhodium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of racemic secondary allylic trichloroacetimidates with a variety of N-methyl anilines, providing allylic N-methyl arylamines in high yields, regioselec
Rhodium-catalyzed regioselective amination of secondary allylic trichloroacetimidates with unactivated aromatic amines
Arnold, Jeffrey S.,Stone, Robert F.,Nguyen, Hien M.
supporting information; experimental part, p. 4580 - 4583 (2010/12/24)
The use of unactivated aromatic amines in the rhodium-catalyzed regioselective amination of secondary allylic trichloroacetimidates is explored. The desired N-arylamines are obtained in high yields and regioselectivity, favoring the branched amination pro
