Shao Bing-Ru, Ren Bai-Hao, Jiang Wen-Feng, Shi Lei
School of Chemistry, Dalian University of Technology, Dalian 116024, P. R. China.
Org Lett. 2024 Apr 5;26(13):2646-2650. doi: 10.1021/acs.orglett.4c00722. Epub 2024 Mar 26.
A successful synthesis of helical-shaped axially chiral bisoxime ethers is reported. This approach utilized symmetric L-shaped diketone scaffolds as carbonyl components for the enantioselective condensation with hydroxylamines, delivering dual axially chiral oxime ethers with up to 99% ee. Additionally, the axially chiral mono-oxime ethers of azabicyclic ketones with high ee's were also successfully produced. Various chiral bicyclic lactams can be readily synthesized via Beckmann rearrangement, demonstrating a potential application in organic synthetic chemistry.
报道了一种螺旋状轴向手性双肟醚的成功合成方法。该方法利用对称的L形二酮支架作为羰基组分，与羟胺进行对映选择性缩合，得到对映体过量高达99%的双轴向手性肟醚。此外，还成功制备了对映体过量较高的氮杂双环酮的轴向手性单肟醚。通过贝克曼重排可以很容易地合成各种手性双环内酰胺，展示了其在有机合成化学中的潜在应用。
