COAP‐Palladium‐catalyzed Asymmetric Linear Allylic Alkylation of Vinyl Benzoxazinanones for Multifunctional 3,3′‐Disubstituted Oxindole Derivatives
COAP‐Palladium‐catalyzed Asymmetric Linear Allylic Alkylation of Vinyl Benzoxazinanones for Multifunctional 3,3′‐Disubstituted Oxindole Derivatives
复制标题
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
DOI：
10.1002/adsc.202201404
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
Xing
中科院分区：
文献类型：
--
作者：
Jun;Sheng;Baishun Wang;Wen;Zheng Wang;Xing
报道了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.合成了一系列具有光学活性的多功能3，3 ′-二取代羟吲哚衍生物，它们分别带有一个季立体中心和一个直链芳氨基侧链，产率为55-98%，对3-（杂）芳基取代羟吲哚的ee为96- 99%。实验结果表明，COAP配体可以作为一种特殊的手性配体，构建具有氮杂、硫代或全碳等四元立体中心的3，3-二取代吲哚类化合物.该方法的显著特点包括底物范围广、无N-保护基、无碱、高区域选择性和对映选择性。
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%eefor 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 asaza‐,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.