钯催化对映选择性分子内Heck羰基化反应：2-氧化吲哚炔酮和羧酸的不对称合成
Palladium-Catalyzed Enantioselective Intramolecular Heck Carbonylation Reactions: Asymmetric Synthesis of 2-Oxindole Ynones and Carboxylic Acids.
作者信息
Zhang Di, Xiong Youyuan, Guo Yingjie, Zhang Lei, Wang Zheng, Ding Kuiling
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
University of Chinese Academy of Sciences, Beijing 100049 (P. R. China), Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, P. R. China.
出版信息
Chemistry. 2022 Jan 3;28(1):e202103670. doi: 10.1002/chem.202103670. Epub 2021 Oct 21.
Herein, we report a Pd-catalyzed enantioselective domino Heck carbonylation reaction of o-iodoacrylanilides with terminal alkynes and water as the nucleophiles, affording a diversity of β-carbonylated 2-oxindole derivatives bearing a 3,3-disubstituted all-carbon quaternary stereocenter, in high yields (55-99 %) with good to excellent enantioselectivities (up to 99 % ee). The synthetic utilities of the protocol were demonstrated in the gram-scale synthesis of 2-oxindole-derived ynone 3 ea and carboxylic acid 4 a, as well as the facile synthesis of chiral 2-oxindoles with a pyrazole or isoxazole moiety.
在此，我们报道了一种钯催化的邻碘丙烯酰苯胺与末端炔烃和水作为亲核试剂的对映选择性多米诺 Heck 羰基化反应，该反应能高产率（55 - 99%）地提供多种带有 3,3 - 二取代全碳季碳立体中心的 β - 羰基化 2 - 氧化吲哚衍生物，对映选择性良好至优异（高达 99% ee）。该方法的合成实用性在 2 - 氧化吲哚衍生的炔酮 3ea 和羧酸 4a 的克级合成以及带有吡唑或异恶唑部分的手性 2 - 氧化吲哚的简便合成中得到了证明。
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