金鸡纳
对映选择合成
立体中心
化学
金鸡纳生物碱
酰胺
催化作用
立体选择性
有机化学
生物碱
组合化学
作者
Shuichi Nakamura,Masato Kibe,Tsunayoshi Takehara,Takeyuki Suzuki
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-02-07
卷期号:25 (6): 1040-1044
标识
DOI:10.1021/acs.orglett.3c00259
摘要
The first enantioselective reaction of α-isocyanoacetonitriles was developed. The reaction of various α-isocyanoacetonitriles with ketimines using cinchona alkaloid amide-Cu(II) catalysts afforded imidazolines with consecutive tetrasubstituted stereogenic carbon centers in good yields and high diastereo- and enantioselectivities. The stereoselectivity of the reaction is explained on the basis of the control experiment and density functional theory (DFT) calculations. The products were subsequently converted into chiral compounds. This process highlights the possible use of α-isocyanoacetonitriles for asymmetric and organic syntheses.
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