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

• DOI: 10.1021/jacs.1c12723
• Publication Date: 2022-02-10T17:45:15Z
• Authors: Bingfei Peng; Jiguo Ma; Jianhua Guo; Yating Gong; Ronghao Wang; Yi Zhang; Jinlong Zeng; Wen-Wen Chen; Kuiling Ding; Baoguo Zhao
• Keywords: 01 natural sciences; 0104 chemical sciences

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.