还原胺化
胺化
铱
化学
组合化学
烷基
还原消去
位阻效应
胺气处理
磷酰胺
催化作用
不对称氢化
氢化物
对映选择合成
有机化学
氢
DNA
生物化学
寡核苷酸
作者
Zitong Wu,Wenji Wang,Haodong Guo,Guorui Gao,Hefei Huang,Mingxin Chang
标识
DOI:10.1038/s41467-022-31045-5
摘要
Direct asymmetric reductive amination is one of the most efficient methods for the construction of chiral amines, in which the scope of the applicable amine coupling partners remains a significant challenge. In this study we describe primary alkyl amines effectively serve as the N-sources in direct asymmetric reductive amination catalyzed by the iridium precursor and sterically tunable chiral phosphoramidite ligands. The density functional theory studies of the reaction mechanism imply the alkyl amine substrates serve as a ligand of iridium strengthened by a (N)H-O(P) hydrogen-bonding attraction, and the hydride addition occurs via an outer-sphere transition state, in which the Cl-H H-bonding plays an important role. Through this concise procedure, cinacalcet, tecalcet, fendiline and many other related chiral amines have been synthesized in one single step with high yields and excellent enantioselectivity.
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