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.
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