化学
对映选择合成
废止
催化作用
亚胺
吲哚试验
有机化学
氨基酯
组合化学
立体化学
作者
Chuan‐Chuan Wang,Jian Huang,Xin‐Hao Li,Søren Kramer,Guo‐Qiang Lin,Xing‐Wen Sun
出处
期刊:Organic Letters
[American Chemical Society]
日期:2018-05-07
卷期号:20 (10): 2888-2891
被引量:26
标识
DOI:10.1021/acs.orglett.8b00927
摘要
The highly enantioselective preparation of spirooxindoles bearing α,α-disubstituted α-amino-β-keto esters was achieved through [4 + 1] annulation of oxindoles and α-imine-β-oxo-γ,δ-unsaturated esters under mild conditions in good yields (up to 82%) and stereoselectivities (up to >20:1 dr, 96% ee). The reaction is amenable to gram scale synthesis using catalyst loading as low as 1 mol %. The corresponding chiral α,α-disubstituted α-amino-β-keto esters could be easily transformed into cyclopenta[b]indole derivatives without erosion of enantiopurity.
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