Allylic rearrangement

Organic chemistry

Amination

Protonation

Enantioselective synthesis

Catalysis

Medicinal chemistry

Chemistry

Enol

Silyl ether

Alkyl

Silylation

Organocatalysis

Brønsted–Lowry acid–base theory

Sulfonyl

Journal of the American Chemical Society

A new type of chiral super Brønsted C–H acids, BINOL-derived phosphoryl bis((trifluoromethyl)sulfonyl) methanes (BPTMs), were developed. As compared to widely utilized BINOL-derived chiral phosphoric acids (BPAs) and N-triflyl phosphoramides (NTPAs), BPTMs displayed much higher Brønsted acidity, resulting in dramatically improved activity and excellent enantioselectivity as demonstrated in catalytic asymmetric Mukaiyama–Mannich reaction, allylic amination, three-component coupling of allyltrimethylsilane with 9-fluorenylmethyl carbamate and aldehydes, and protonation of silyl enol ether. These new strong Brønsted C–H acids have provided a platform for expanding the chemistry of asymmetric Brønsted acid catalysis.

A Powerful Chiral Super Brønsted C–H Acid for Asymmetric Catalysis