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首页> 外文期刊>Chemistry: A European journal >A Solid-Supported Organocatalyst for Highly Stereoselective, Batch, andContinuous-Flow Mannich Reactions
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A Solid-Supported Organocatalyst for Highly Stereoselective, Batch, andContinuous-Flow Mannich Reactions

机译：固体支持的有机催化剂，用于高度立体选择性，间歇和连续流曼尼希反应

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摘要

The fast and highly stereose-lective Mannich reaction of aldehydesand ketones with the N-(p-methoxy-phenyl) ethyl glyoxylate imine cata-lyzed by polystyrene resins functional-ized with (2S,4R)-hydroxyproline is re-ported. The effect of the nature of thelinker connecting proline with the poly-meric backbone has been studied, anda 1,2,3-triazole linker constructed fromazidomethyl polystyrene and 0-prop-argyl hydroxyproline turns out to beoptimal for catalytic activity and enan-tioselectivity. With aldehyde donors,fast reactions leading to complete con- version in 1-3 h are recorded in DMF.With ketone donors, the reactions tendto be slower, but can be efficiently ac-celerated (six-membered ring cycloal-kanones) by low-power microwave ir-radiation. This approach, which greatlyfacilitates product isolation since thecatalyst is removed by simple filtration,has allowed the implementation of thereactions of aldehyde substrates in a continuous-flow, single-pass system. Inthis manner, the continuous synthesisof the enantiomerically and diastereo-merically pure adducts (syn/anti > 97:3;ee > 99%) has been achieved at roomtemperature with residence times of6.0 min. This methodology has allowedfor the preparation of up to 7.8 mmolof the desired Mannich adduct throughthe use of 0.46 mmol of catalytic resin(5.9 mol%), in a greatly simplified ex-perimental protocol that avoids purifi-cation steps.
机译：报告了醛和酮与N-（对甲氧基苯基）乙醛酸亚乙基酯亚胺的快速和高度立体选择反应，该反应由（2S，4R）-羟基脯氨酸官能化的聚苯乙烯树脂催化。已经研究了连接脯氨酸与多聚主链的连接基的性质的影响，并且由叠氮基甲基聚苯乙烯和0-丙炔基羟基脯氨酸构建的1,2,3-三唑连接基对于催化活性和对映体选择性是最佳的。使用醛供体时，在DMF中记录了可在1-3小时内完成完全转化的快速反应。使用酮供体时，反应速度较慢，但​​可通过较低的速度有效地促进（六元环环加酮）。功率微波辐照。由于通过简单的过滤除去了催化剂，该方法极大地促进了产物的分离，该方法允许在连续流，单程系统中实施醛底物的反应。以这种方式，在室温下以6.0分钟的停留时间实现了对映体和非对映体纯的加合物（syn / anti> 97：3; ee> 99％）的连续合成。该方法通过大大简化的避免纯化步骤的实验方案，通过使用0.46 mmol的催化树脂（5.9 mol％）可以制备高达7.8 mmol的所需曼尼希加合物。

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