1454933-35-7Relevant academic research and scientific papers
Click-binol-phosphoric acid catalysts in intramolecular enantioselective oxidative C[sbnd]H-bond functionalization
Stockerl, Sebastian,Gutiérrez, Daniel,García Manche?o, Olga
, p. 572 - 585 (2016/12/16)
Counteranion-catalysis represents an appealing but challenging approach for the development of enantioselective oxidative C[sbnd]H bond functionalization reactions. In this work, a new family of 3,3′-triazolyl BINOL-derived phosphoric acids was synthesized and employed in the intramolecular asymmetric C[sbnd]H bond functionalization of N-aryl substituted tetrahydroisoquinolines. As previously reported with related structures, the presence of the triazole groups on the catalysts was key to attain enantioselectivity. Our study also shows the importance of choosing the appropriate regioisomeric triazole groups at the BINOL backbone to achieve a more efficient chirality transfer. Moderate enantiomeric ratios were obtained with the N-benzamide substrates, whereas the change of the nature of the nucleophile fragment was translated to a dramatic loss of the enantioselectivity. Therefore, it can be foreseen that there is a need for designing further superior catalyst structures to develop future counter-anion organocatalyzed asymmetric C[sbnd]H bond functionalization reactions.
Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids
Neel, Andrew J.,Hehn, Joerg P.,Tripet, Pascal F.,Toste, F. Dean
supporting information, p. 14044 - 14047 (2013/10/21)
This report describes the development of an enantioselective C-N bond-forming reaction to produce 1,2,3,4-tetrahydroisoquinoline-derived cyclic aminals catalyzed by chiral phosphate anions. Central to the success of this goal was the design of a library of 3,3′-triazolyl BINOL-derived phosphoric acids capable of forming attractive hydrogen-bonding interactions with the peptide-like substrate. We envision this work will offer an alternative to the conventional strategy of increasing catalyst steric bulk to improve enantioselectivity with BINOL-derived phosphoric acids.
