Catalytic enantioselective Pudovik reaction of aldehydes and aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex.
New chiral tethered bis(8-quinolinolato) (TBOx) aluminum(III) complexes effectively catalyze the addition of phosphites to aldehydes and aldimines to give enantioenriched alpha-hydroxy and alpha-amino phosphonates in high yields and enantioselectivities with unprecedented reactivity (TON =100 as high as 200). The catalyst is optimized with the low catalyst loading of 0.5 - 1.0 mol %. The modular synthesis of the catalyst allows for potential to tune the reaction for maximum catalytic activity. To date there are few examples with broad substrate scopes that can catalyze both aldehydes and aldimines with such high selectivity and no reports utilizing such low catalyst loading.
Abell
Joshua P
JP
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Yamamoto
Hisashi
H