Abstract

Chiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%) and excellent enantioselectivities (ee up to 99%). The highest enantioselectivity (ee 99%) was obtained with p-trifluorobenzaldehyde as the substrate containing the strongly electron-acceptor CF₃ group.

中文翻译：

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使用新型噻吩基手性配体将二乙基锌对映体加成到芳香醛上

摘要

由噻吩甲醛（甲基或乙基取代的）和手性氨基醇（如去氧麻黄碱和2-氨基丙醇的对映异构体）合成具有噻吩部分的手性去氧麻黄碱衍生的β-氨基醇。将合成的配体用于将二乙基锌催化不对称加成到醛中，从而获得具有高转化率（92％）和出色的对映选择性（ee高达99％）的旋光醇。用对-三氟苯甲醛作为含有强电子受体CF ₃基团的底物可获得最高的对映选择性（ee 99％）。