COAP-Palladium-Catalyzed Asymmetric Linear Allylic Alkylation of Vinyl Benzoxazinanones for Multifunctional 3,3′-Disubstituted Oxindole Derivatives,Advanced Synthesis & Catalysis

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COAP-Palladium-Catalyzed Asymmetric Linear Allylic Alkylation of Vinyl Benzoxazinanones for Multifunctional 3,3′-Disubstituted Oxindole Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2023-03-15 , DOI: 10.1002/adsc.202201404
Jun-Hao Shen ₁ , Sheng-Suo Zhou ₁ , Bai-Lin Wang ₁ , Wen-Kai Liu ₁ , Zheng Wang ₂ , Xing-Wang Wang ₁

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A Pd-catalyzed enantioselective linear-allylic alkylation of vinyl benzoxazinanones with a series of 3-substituted oxindoles was reported in the presence of a chiral oxamide-phosphine ligand (COAP−Bn) under mild reaction conditions. A series of optically active multifunctional 3,3′-disubstituted oxindole derivatives bearing a quaternary stereogenic center and a linear aryl amino side chain were respectively obtained in 55–98% yields with 96–99% ee for 3-(hetero)aryl substituted oxindoles. The developed protocol demonstrates that the COAP ligands could serve as a privileged chiral ligand to construct diverse chiral 3,3-disubstituted oxindole compounds with various quaternary stereogenic centers, such as aza-, thio- or all-carbon quaternary stereogenic centers. The salient features of the method include broad substrate scope, N-protecting group free, base-free, and high regio- and enantioselectivity.

中文翻译：

COAP-钯催化乙烯基苯并恶嗪酮的不对称线性烯丙基烷基化制备多功能 3,3'-二取代羟吲哚衍生物

据报道，在温和反应条件下，在手性草酰胺-膦配体 (COAP-Bn) 存在下，Pd 催化的乙烯基苯并恶嗪酮与一系列 3-取代羟吲哚的对映选择性线性-烯丙基烷基化反应。一系列具有季立体异构中心和线性芳基氨基侧链的光学活性多功能 3,3'-二取代羟吲哚衍生物分别以 55-98% 的产率和 96-99% ee 的3-（杂）芳基取代羟吲哚获得. 开发的方案表明，COAP 配体可以作为一种特殊的手性配体来构建具有各种季立体异构中心（如氮杂-、硫代）的多种手性 3,3-二取代羟吲哚化合物- 或全碳季立体中心。该方法的显着特点包括广泛的底物范围、无N-保护基、无碱基以及高区域选择性和对映选择性。

更新日期：2023-03-15

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