化学
氨基酸
反应性(心理学)
席夫碱
丙氨酸
基础(拓扑)
立体化学
催化作用
对映选择合成
组合化学
有机化学
病理
替代医学
数学分析
医学
生物化学
数学
作者
Maximilian Bremerich,Carsten Bolm,Gerhard Raabe,Vadim A. Soloshonok
标识
DOI:10.1002/ejoc.201700339
摘要
N ‐(2‐Benzoylphenyl)‐2‐( tert ‐butylamino)propanamide has been designed as an advanced chiral auxiliary for the general asymmetric synthesis of α‐amino acids by in situ formation of the corresponding Schiff bases with amino acids followed by complexation with Ni II ions and base‐catalyzed thermodynamic equilibrium. The first discovery stage described in this work has been focused on the exploration of stereocontrolling properties of the compound as a function of the reaction conditions and structural facets of various α‐amino acids. By using reactions with unprotected α‐amino acids as a model process, it was found that the corresponding Schiff base–Ni II complexes were formed in a straightforward manner with both good to excellent chemical yields (73–99 %) and diastereoselectivity (74–26 to >98–2). The observed stereochemical outcome bodes well with the wide synthetic applications of this new type of 2‐( tert ‐butylamino)propanamide‐derived chiral auxiliary.
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