通过有机催化级联迈克尔/羟醛缩合反应对三氟甲基取代环己酮的对映选择性合成。
Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction.
机构信息
College of Chemistry and Environment Protection Engineering, Southwest Minzu University, Chengdu 610041, China.
Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University, Chengdu 610031, China.
出版信息
Org Biomol Chem. 2020 Feb 26;18(8):1607-1611. doi: 10.1039/d0ob00004c.
An enantioselective (92-99% ee) Michael/aldol cascade reaction between 4,4,4-trifluoroacetoacetates and α,β-unsaturated enones was established in the presence of cinchona alkaloid-based primary amines. Various β-CF3-cyclohexanones were constructed in high yields (81-99%) as a couple of separable diastereomers. This tandem reaction was sensitive to acidic co-catalysts, with a Michael/aldol condensation process favorably occurring to generate β-CF3-cyclohexenones (42-69% yield, 84-96% ee) in the presence of trifluoroacetic acid.
在金鸡纳生物碱衍生的伯胺存在下，建立了 4,4,4-三氟乙酰乙酸酯和α,β-不饱和烯酮之间的对映选择性（92-99%ee）迈克尔/Aldol 级联反应。各种β-CF3-环己酮作为一对可分离的非对映异构体以高产率（81-99%）构建。该串联反应对酸性共催化剂敏感，在三氟乙酸存在下，迈克尔/Aldol 缩合过程有利于生成β-CF3-环己烯酮（42-69%产率，84-96%ee）。
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