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Synthesis of Helical-Shaped Axially Chiral Bisoxime Ethers via Chiral Phosphoric-Acid-Catalyzed Sequential Enantioselective Condensations
Organic Letters ( IF 5.2 ) Pub Date : 2024-03-26 , DOI: 10.1021/acs.orglett.4c00722
Bing-ru Shao 1 , Bai-hao Ren 1 , Wen-feng Jiang 1 , Lei Shi 1
Affiliation  

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.

中文翻译:

手性磷酸催化顺序对映选择性缩合合成螺旋状轴向手性双肟醚

据报道,成功合成了螺旋形轴向手性双肟醚。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,产生对映体含量高达 99% 的双轴手性肟醚。此外,还成功制备了具有高ee值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,这证明了其在有机合成化学中的潜在应用。
更新日期:2024-03-26
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