Multiple Hydrogen-Bond Activation in Asymmetric Brønsted Acid Catalysis

1 Lewis Acid – Brønsted Base Catalysis

From the synthetic point of view, organic synthesis via catalytic processes offers many benefits. Catalysis frequently obviates the excessive use of the activating reagents and associated tedious purification processes, thereby offering more environmentally benign synthetic processes. Furthermore, the specific activation mode of a catalyst allows for highly chemoselective transformations that a...

Internal Lewis Acid Assisted Single Hydrogen Bond Donor Catalysis

NMR Spectroscopic Characterization of Charge Assisted Strong Hydrogen Bonds in Brønsted Acid Catalysis

Hydrogen bonding plays a crucial role in Brønsted acid catalysis. However, the hydrogen bond properties responsible for the activation of the substrate are still under debate. Here, we report an in depth study of the properties and geometries of the hydrogen bonds in (R)-TRIP imine complexes (TRIP: 3,3'-Bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogen phosphate). From NMR spectro...

Asymmetric cooperative catalysis of strong Brønsted acid-promoted reactions using chiral ureas.

Cationic organic intermediates participate in a wide variety of useful synthetic transformations, but their high reactivity can render selectivity in competing pathways difficult to control. Here, we describe a strategy for inducing enantioselectivity in reactions of protio-iminium ions, wherein a chiral catalyst interacts with the highly reactive intermediate through a network of noncovalent i...

Efficient hydration of alkynes through acid-assisted Brønsted acid catalysis.

The combined acid catalyzed hydration of alkynes is an efficient one-step synthesis of carbonyl compounds. This atom-economical method is effective with a wide range of substrates, and the products are obtained in very good yields with low catalyst loading (0.2%). Furthermore, solid acids like Nafion were also efficient and could be easily recycled multiple times without loss of reactivity.