A Powerful Chiral Super Brønsted C–H Acid for Asymmetric Catalysis,Journal of the American Chemical Society

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A Powerful Chiral Super Brønsted C–H Acid for Asymmetric Catalysis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-02-10 , DOI: 10.1021/jacs.1c12723
Bingfei Peng ₁ , Jiguo Ma _{1,

2} , Jianhua Guo ₁ , Yating Gong ₁ , Ronghao Wang ₁ , Yi Zhang _{1,

2} , Jinlong Zeng ₁ , Wen-Wen Chen ₁ , Kuiling Ding ₂ , Baoguo Zhao ₁

Affiliation

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.

中文翻译：

用于不对称催化的强大手性超级布朗斯台德 C-H 酸

开发了一种新型手性超级布朗斯台德 C-H 酸，即 BINOL 衍生的磷酸双（（三氟甲基）磺酰基）甲烷 (BPTMs)。与广泛使用的 BINOL 衍生的手性磷酸 (BPA) 和N -triflyl 磷酰胺 (NTPAs) 相比，BPTM 表现出更高的布朗斯台德酸度，从而显着提高活性和优异的对映选择性，如催化不对称 Mukaiyama-Mannich 反应、烯丙基胺化，烯丙基三甲基硅烷与 9-芴基甲基氨基甲酸酯和醛的三组分偶联，以及甲硅烷基烯醇醚的质子化。这些新的强 Brønsted C-H 酸为扩展不对称 Brønsted 酸催化的化学性质提供了一个平台。

更新日期：2022-02-10

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