Chang Kedi, Chou Ruilong, Yu Pinke, Zuo Linhong, Liu Qixing, Zhang Xumu, Yin Congcong, Zhou Haifeng
Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, 443002, China.
Department of Chemistry, Academy for Advanced Interdisciplinary Studies and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, 518055, China.
Chemistry. 2024 Dec 10;30(69):e202403055. doi: 10.1002/chem.202403055. Epub 2024 Oct 31.
A straightforward asymmetric transfer hydrogenation for accessing enantiomerically enriched secondary benzyl alcohols involving free phenolic hydroxyl group(s) under mild conditions was developed. Various of optical pure aryl alcohols with a remarkable functional group compatibility were achieved with 78 %-97 % yields, 84 %->99 % ee's and up to 10 000 TON. This rhodium-catalyzed reaction could be performed in a gram-scale without loss of the efficiency. Furthermore, the synthetic utility has also been demonstrated in the asymmetric synthesis of (S)-adrenaline and (S)-phenylephrine.
开发了一种直接的不对称转移氢化方法，可在温和条件下制备含有游离酚羟基的对映体富集仲苄醇。该方法以78%-97%的产率、84%->99%的对映体过量（ee值）以及高达10000的转化数（TON），实现了各种具有出色官能团兼容性的光学纯芳醇。这种铑催化反应能够以克级规模进行且效率不损失。此外，该方法在（S）-肾上腺素和（S）-去氧肾上腺素的不对称合成中也展示了其合成实用性。
