对映体药物
不对称氢化
营业额
催化作用
酮
生物催化
化学
对映体过量
有机化学
对映选择合成
对映体
组合化学
反应机理
作者
Congcong Yin,Yafei Jiang,Fanping Huang,Cong Xu,Yingmin Pan,Shuang Gao,Gen‐Qiang Chen,Xiaoqing Ding,Shao‐Tao Bai,Qiwei Lang,Jun Li,Xumu Zhang
标识
DOI:10.1038/s41467-023-39375-8
摘要
Abstract Developing catalysts with both useful enantioselectivities and million turnover numbers (TONs) for asymmetric hydrogenation of ketones is attractive for industrial production of high-value bioactive chiral entities but remains a challenging. Herein , we report an ultra-efficient anionic Ir-catalyst integrated with the concept of multidentate ligation for asymmetric hydrogenation of ketones. Biocatalysis-like efficacy of up to 99% ee (enantiomeric excess), 13,425,000 TON (turnover number) and 224 s −1 TOF (turnover frequency) were documented for benchmark acetophenone. Up to 1,000,000 TON and 99% ee were achieved for challenging pyridyl alkyl ketone where at most 10,000 TONs are previously reported. The anionic Ir-catalyst showed a novel preferred ONa/MH instead of NNa/MH bifunctional mechanism. A selective industrial route to enantiopure nicotine has been established using this anionic Ir-catalyst for the key asymmetric hydrogenation step at 500 kg batch scale, providing 40 tons scale of product.
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