College of Biotechnology and Pharmaceutical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, 30 Puzhu Rd S, Nanjing, 211816, China.
Chem Commun (Camb). 2021 Apr 7;57(27):3379-3382. doi: 10.1039/d0cc07995b. Epub 2021 Mar 8.
A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu(i) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.
发展了一种铜催化的丙二酸酯桥连酰基肟与色酮的区域选择性[3+2]环加成反应，以中等至良好的收率和优异的非对映选择性得到了有价值的 2,3-二氢恶唑螺[吲哚啉]。该反应序列涉及 Cu(i)引发的 N-O 键断裂、1,5-HAT 和 C-N 键形成。该方案具有温和的反应条件和广泛的底物范围。DFT 计算表明，[3+2]环加成途径在动力学和热力学上都更有利。
