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首页> 外文期刊>Chemistry: A European journal >Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines
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Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines

机译：由α-手性胺制备的亚胺催化不对称叠氮化中的双立体分化

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摘要

The catalytic asymmetric aziridination of imines and diazo compounds (AZ reaction) mediated by boroxinate catalysts derived from the VANOL and VAPOL ligands was investigated with chiral imines derived from five different chiral, disubstituted, methyl amines. The strongest matched and mismatched reactions with the two enantiomers of the catalyst were noted with disubstituted methyl amines that had one aromatic and one aliphatic substituent. The synthetic scope for the AZ reaction was examined in detail for α-methylbenzyl amine for cis-aziridines from α-diazo esters and for trans-aziridines from α-diazo acetamides. Optically pure aziridines could be routinely obtained in good yields and with high diastereoselectivity and the minor diastereomer (if any) could be easily separated. The matched case for cis-aziridines involved the (R)-amine with the (S)-ligand, but curiously, for trans-aziridines the matched case involved the (R)-amine with the (R)-ligand for imines derived from benzaldehyde and n-butanal, and the (R)-amine with the (S)-ligand for imines derived from the bulkier aliphatic aldehydes pivaldehyde and cyclohexane carboxaldehyde.
机译：用衍生自VANOL和VAPOL配体的硼辛酸酯催化剂介导的亚胺和重氮化合物的催化不对称叠氮化（AZ反应）与衍生自五种不同手性二取代甲胺的手性亚胺进行了研究。用具有一个芳族和一个脂族取代基的二取代甲胺注意到与催化剂的两种对映异构体最强的匹配和错配反应。详细检查了AZ反应的合成范围，其中包括α-重氮酯的顺式氮丙啶和α-重氮乙酰胺的反式氮丙啶的α-甲基苄基胺。通常可以以高收率和高非对映选择性常规获得光学纯的氮丙啶，并且可以容易地分离次要非对映异构体（如果有的话）。顺式氮丙啶的匹配案例涉及（R）-胺与（S）-配体，但奇怪的是，对于反式氮丙啶，匹配的案例涉及（R）-胺与（R）-配体的亚胺衍生自苯甲醛和正丁醛，以及（R）-胺与（S）-配体的亚胺，衍生自体积较大的脂族醛，戊醛和环己烷羧醛。

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