Catalytic Enantioselective Aza-pinacol Rearrangement
Catalytic Enantioselective Aza-pinacol Rearrangement
复制标题
催化对映选择性氮杂频哪醇重排
DOI：
10.1002/anie.201705539
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发表时间：
2017
影响因子：
16.6
通讯作者：
Zu Liansuo
中科院分区：
文献类型：
--
作者：
Yu Yuanyuan;Li Jingwen;Jiang Long;Zhang Jing-Ren;Zu Liansuo
报道了第一个催化的对映选择性不对称氮杂频哪醇重排反应。该反应由手性磷酸催化，并通过涉及环状氮杂-邻-亚二甲苯基中间体的高度有序的过渡态进行，以提供具有良好至优异的对映选择性的吲哚啉结构。该方法的合成效用通过天然产物明非辛的关键中间体的不对称合成和抑制抗生素耐药性的手性先导化合物的鉴定来证明。
The first catalytic enantioselective asymmetric aza‐pinacol rearrangement is reported. The reactions are catalyzed by a chiral phosphoric acid and proceed via a highly organized transition state involving a cyclic aza‐ortho‐xylylene intermediate to afford the indoline structures with good to excellent enantioselectivity. The synthetic utility of this method is demonstrated by the asymmetric synthesis of a key intermediate to the natural product minfiensine and the identification of a chiral lead compound to repress antibiotic resistance.