New class of P-stereogenic chiral Brønsted acid catalysts derived from chiral phosphinamides.

• New class of P -stereogenic chiral N H Brønsted acid organocatalysts prepared. • Catalysts were prepared from chiral phosphinamides or secondary phosphine oxides. • Catalysts promoted the asymmetric reduction of quinolones by transfer hydrogenation. • Asymmetric transformation effected by the P -stereogenic chiral environment. • Easily tunable selectivity and reactivity by the substituents of phosphorous. A new class of N H Brønsted acid organocatalysts that feature P -stereogenic chirality was developed. These catalysts were prepared from P -stereogenic chiral phosphinamides and show similar reactivity to BINOL derived phosphoric acid toward the reduction of quinolines via transfer hydrogenation. It shows that stereoselectivity is induced by the P -chiral environment that is created by the substituents attached to the phosphorous atom, which can be readily tuned and modified. [ABSTRACT FROM AUTHOR]