Heterogeneous Catalysts for Racemization and Dynamic Kinetic Resolution of Amines and Secondary Alcohols
Heterogeneous Catalysts for Racemization and Dynamic Kinetic Resolution of Amines and Secondary Alcohols
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DOI：
10.1007/s11244-010-9512-x
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发表时间：
2010-08-01
影响因子：
3.6
通讯作者：
De Vos, Dirk
中科院分区：
文献类型：
--
作者：
Parvulescu, Andrei;Janssens, Joost;De Vos, Dirk
综述了手性稳定的仲醇和胺的非均相外消旋化催化剂，以及这些催化剂与固定化酶在动态动力学拆分（DKR）下合成对映纯酯或酰胺的研究进展。对于一锅DKR工艺，酶和多相催化剂的相容性是一个主要问题，在某些情况下，由于（相互）失活，组合失败。各种类型的非均相催化剂，如沸石或氧化物影响醇外消旋；它们要么通过酸催化和正碳化学作用，要么通过酮的氧化还原途径起作用。然而，在温和条件下使用多相催化剂进行脂肪族醇的动态动力学拆分是一个开放的挑战。异相胺外消旋催化剂总是通过亚胺的氧化还原机制进行操作。在这种情况下，范围包括苯胺和脂肪胺。该方法的实用性通过生产对映纯n -酰化的同丝氨酸内酯来说明，这是微生物群落中的信号化合物。
This paper gives an overview of the available heterogeneous catalysts for racemization of chirally stable secondary alcohols and amines, and of the combination of these catalysts with immobilized enzymes in dynamic kinetic resolution (DKR) for production of enantiopure esters or amides. For the one-pot DKR process, compatibility of enzyme and heterogeneous catalyst is a major issue, and in some cases the combination fails because of (mutual) deactivation. Heterogeneous catalysts of various types, such as zeolites or oxides effect alcohol racemization; they function either via acid catalysis and carbenium chemistry, or via a redox pathway via the ketone. Dynamic kinetic resolution of aliphatic alcohols using a heterogeneous catalyst in mild conditions is however an open challenge. Heterogeneous amine racemization catalysts invariably operate using a redox mechanism via the imine. In this case, the scope encompasses benzylic and aliphatic amines. The practicality of the approach is illustrated with the production of enantiopure N-acylated homoserine lactones, which are signalling compounds in microbial communities.