Changing of Paradigm for Enantioselective Organocatalysis with Brønsted Acids: Synthesis and Application of Original P-Chirogenic Organocatalysts – P-ChiroCat

Since the pioneering work of Akiyama and Terada in 2004 on BINOL-derived chiral phosphoric acids, a huge amount of efforts worldwide has been devoted to the development of elaborated C2-axially chiral catalysts including sterically crowded atropisomeric BINOL, VAPOL or spirocyclic SPINOL derivatives. Although, successful in many inter- or intramolecular transformations involving activation of iminium or oxocarbenium ions, the scale up and the potential industrial development of this family of catalysts is hampered by a low variability and in most cases a tedious multistep synthetic access. The P-ChiroCat project has the ambition of changing the over-ten-years-old C2-axially chiral paradigm by proposing an original and complementary design for simple and easily accessible Brønsted acids in which the chirality is now centered on the phosphorus atom opening new synthetic opportunities for both hydrogen-bonding and ion-pairing enantioselective organocatalyses.