Asymmetric NHC-catalyzed redox α-amination of α-aroyloxyaldehydes.
Asymmetric α-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N-N bond cleavage.
EaStCHEM, School of Chemistry, University of St Andrews , North Haugh, St Andrews, KY16 9ST, United Kingdom.
James E
JE
Taylor
David S B
DS
Daniels
Andrew D
AD
Smith
D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006571:Heterocyclic Compounds / Q000737:chemistry; D006834:Hydrazines / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012493:Samarium / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D006571:Heterocyclic Compounds; D006834:Hydrazines; D007454:Iodides; C030011:carbene; D012493:Samarium; C409809:samarium diiodide; D008697:Methane