Kumar Rohtash, Maurya Vidyasagar, Avinash Avinash, Appayee Chandrakumar
Department of Chemistry, Indian Institute of Technology Gandhinagar, Palaj, Gandhinagar, Gujarat 382055, India.
J Org Chem. 2024 Jun 21;89(12):8586-8600. doi: 10.1021/acs.joc.4c00523. Epub 2024 Jun 5.
The first chiral synthesis of nonsilyl bicyclic secondary amine organocatalysts and their application to the asymmetric transfer hydrogenation of α,β-unsaturated aldehydes are disclosed. A lower catalytic loading (5 mol %) is demonstrated for the reduction of a wide range of α,β-unsaturated aldehydes (up to 97% yield and up to 99% ). The application of this scalable methodology is showcased for the asymmetric synthesis of bioactive molecules such as phenoxanol, citronellol, ramelteon, and terikalant.
首次公开了非硅基双环仲胺有机催化剂的手性合成及其在α,β-不饱和醛的不对称转移氢化反应中的应用。结果表明，在还原多种α,β-不饱和醛时，较低的催化负载量（5 mol%）即可实现反应（产率高达97%，对映体过量值高达99%）。该可扩展方法在生物活性分子如苯氧乙醇、香茅醇、雷美替胺和替卡兰的不对称合成中得到了展示。
