化学
立体中心
邻接
动力学分辨率
阿托品
方位(导航)
分辨率(逻辑)
不对称氢化
动能
对映选择合成
立体化学
组合化学
有机化学
催化作用
物理
地图学
量子力学
人工智能
计算机科学
地理
作者
Nianxin Rong,Ao Zhou,Mingrong Liang,Shou‐Guo Wang,Qin Yin
摘要
The asymmetric hydrogenation (AH) of N-unprotected indoles is a straightforward, yet challenging method to access biologically interesting NH chiral indolines. This method has for years been limited to 2/3-monosubstituted or 2,3-disubstituted indoles, which produce chiral indolines bearing endocyclic chiral centers. Herein, we have reported an innovative Pd-catalyzed AH of racemic α-alkyl or aryl-substituted indole-2-acetates using an acid-assisted dynamic kinetic resolution (DKR) process, affording a range of structurally fascinating chiral indolines that contain exocyclic stereocenters with excellent yields, diastereoselectivities, and enantioselectivities. Mechanistic studies support that the DKR process relies on a rapid interconversion of each enantiomer of racemic substrates, leveraged by an acid-promoted isomerization between the aromatic indole and nonaromatic exocyclic enamine intermediate. The reaction can be performed on a gram scale, and the products can be derivatized into non-natural β-amino acids via facile debenzylation and amino alcohol upon reduction.
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