Garai Sumit, Ghosh Krishna Gopal, Biswas Ashik, Chowdhury Sushobhan, Sureshkumar Devarajulu
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, West Bengal 741246, India.
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow-226031, India.
Chem Commun (Camb). 2022 Jul 12;58(56):7793-7796. doi: 10.1039/d2cc03106j.
In this study, we report an efficient protocol for Pd-catalyzed methylene β-C(sp)-H cyanomethylation of 8-aminoquinoline-directed α-amino acids using inexpensive chloroacetonitrile. Iodoacetonitrile generated from chloroacetonitrile reacts with methylene C(sp)-H bonds of α-amino acids with excellent diastereoselectivity, enabling access to a wide range of important γ-cyano-α-amino acids. Our protocol works well with different amino acid and carboxylic acid derivatives with good chemical yields and high functional group tolerance.
在本研究中，我们报道了一种高效的方法，使用廉价的氯乙腈实现钯催化的8-氨基喹啉导向的α-氨基酸的亚甲基β-C(sp)-H氰甲基化反应。由氯乙腈生成的碘乙腈与α-氨基酸的亚甲基C(sp)-H键以优异的非对映选择性反应，能够合成多种重要的γ-氰基-α-氨基酸。我们的方法适用于不同的氨基酸和羧酸衍生物，具有良好的化学产率和高官能团耐受性。
