A Dual-Catalysis Approach to the Asymmetric Steglich Rearrangement and Catalytic Enantioselective Addition of O-Acylated Azlactones to Isoquinolines
A Dual-Catalysis Approach to the Asymmetric Steglich Rearrangement and Catalytic Enantioselective Addition of O-Acylated Azlactones to Isoquinolines
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DOI：
10.1021/ja208156z
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发表时间：
2011-10-26
影响因子：
15
通讯作者：
Seidel, Daniel
中科院分区：
文献类型：
--
作者：
De, Chandra Kanta;Mittal, Nisha;Seidel, Daniel
双催化方法，即非手性亲核催化剂和手性阴离子结合催化剂的组合，应用于Steglich重排，以高度对映选择性的方式提供α， α -二取代氨基酸衍生物。异喹啉的亲核共催化剂取代导致反应途径的分化和前所未有的o-酰化氮杂内酯转化。这种策略提供了高度取代的α， β -二氨基酸衍生物，具有良好的立体控制水平。
A dual-catalysis approach, namely the combination of an achiral nucleophilic catalyst and a chiral anion-binding catalyst, was applied to the Steglich rearrangement to provide alpha,alpha-disubstituted amino acid derivatives in a highly enantioselective fashion. Replacement of the nucleophilic co-catalyst for isoquinoline resulted in a divergent reaction pathway and an unprecedented transformation of O-acylated azlactones. This strategy provided highly substituted alpha,beta-diamino acid derivatives with excellent levels of stereocontrol.