Asymmetric Transfer Hydrogenation of Heterocyclic Compounds in Continuous Flow Using an Immobilized Chiral Phosphoric Acid as the Catalyst

Asymmetric Transfer Hydrogenation of Heterocyclic Compounds in Continuous Flow Using an Immobilized Chiral Phosphoric Acid as the Catalyst
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使用固定化手性磷酸作为催化剂连续流动杂环化合物的不对称转移氢化

DOI:
10.1055/a-2085-5256
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发表时间:
2023
期刊:
Synthesis
影响因子:
--
通讯作者:
Nagorny, Pavel
Nagorny, Pavel
中科院分区:
--
文献类型:
--
作者:
Zhelavskyi, Oleksii;Jhang, Yin-Jia;Nagorny, Pavel

文献摘要

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本文介绍了用固定化手性磷酸催化剂(R)-PS-AdTRIP间歇和连续流动催化双环含氮杂环化合物的转移加氢反应。当流速从0.2mL/min增加到2.0-2.5mL/min时,在填充(R)-PS-AdTRIP的连续床反应器中,对映体选择性有了显著的提高。优化的连续流动条件提供比间歇转移加氢更高的4-6%ee的选择性,其中(R)-PS-AdTRIP的摩尔分数为2mol%,并用于在同一床反应器中生成多个手性产品。
This manuscript describes transfer hydrogenation of bicyclic nitrogen-containing heterocyclic compounds using the immobilized chiral phosphoric acid catalyst (R)-PS-AdTRIP in batch and continuous flow. A significant improvement in enantioselectivities is achieved in continuous flow with a fluidized bed reactor packed with (R)-PS-AdTRIP when the flow rate is increased from 0.2 mL/min to 2.0–2.5 mL/min. The optimized continuous flow conditions consistently provide 4–6% ee higher selectivity than transfer hydrogenation in batch with 2 mol% of (R)-PS-AdTRIP, and are used to generate multiple chiral products with the same fluidized bed reactor.