通过 1,3-偶极环加成反应的非对映选择性合成双螺[氧吲哚-环己酮]吡咯烷。

Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia.

Molecules. 2017 Dec 4;22(12):2134. doi: 10.3390/molecules22122134.

For the first time, arylmethylidene cyclohexanones that are non-symmetrical due to the presence of peripheral substituents were studied in 1,3-dipolar cycloaddition reactions. It is shown that the interaction with the azomethine ylide generated from sarcosine proceeds regio- and diastereoselectively, with the participation of two non-equivalent parts of the dipolarophile. Also for the first time, β-amino ketones (Mannich bases) were used as dipolarophile equivalents of unsaturated ketones. It was found that cycloaddition occurs diastereoselectively at the generated center.

首次研究了由于存在外围取代基而不对称的芳基亚甲基环己酮在 1,3-偶极环加成反应中的作用。结果表明，与从肌氨酸生成的亚甲亚胺叶立德的相互作用具有区域和立体选择性，涉及二极性体的两个不等价部分的参与。同时，首次使用β-氨基酮（曼尼希碱）作为不饱和酮的偶极子等价物。研究发现，在生成的中心发生了立体选择性的环加成反应。