手性吲哚啉-2-羧酸实现了与 4-（溴甲基）环己酮的高对映选择性 Catellani 型环化反应。
Chiral Indoline-2-carboxylic Acid Enables Highly Enantioselective Catellani-type Annulation with 4-(Bromomethyl)cyclohexanone.
机构信息
Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.
出版信息
Angew Chem Int Ed Engl. 2021 Nov 15;60(47):24844-24848. doi: 10.1002/anie.202109771. Epub 2021 Oct 20.
Chiral indoline-2-carboxylic acid has been identified to enable a highly enantioselective Catellani-type annulation of (hetero)aryl, alkenyl triflate and conjugated vinyl iodides with 4-(bromomethyl)cyclohexanone, directly assembling a diverse range of chiral all-carbon bridged ring systems. Control experiments and DFT calculations suggest that the coordinating orientation of the chiral amino acid to the arylpalladium(II) center allows for high levels of stereochemical control.
手性吲哚啉-2-羧酸被确定为能够实现（杂）芳基、烯基三氟甲磺酸酯和共轭乙烯基碘化物与 4-（溴甲基）环己酮的高度对映选择性 Catellani 型环加成，直接组装出各种手性全碳桥环系统。控制实验和 DFT 计算表明，手性氨基酸与芳基钯（II）中心的配位方向允许高水平的立体化学控制。
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