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A chemo-enzymatic oxidation/aldol sequential process directly converts arylbenzyl alcohols and cyclohexanol into chiral β-hydroxy carbonyls
Green Chemistry ( IF 9.8 ) Pub Date : 2021-09-07 , DOI: 10.1039/d1gc02831f
Yu Wang 1 , Chengyi Wang 1 , Qipeng Cheng 1 , Yu Su 1 , Hongyu Li 1 , Rui Xiao 1 , Chunxia Tan 1 , Guohua Liu 1
Affiliation  

The development of a combination enzyme and organocatalyst for aqueous sequential organic transformation has great significance, in that it is not only environmentally friendly but also overcomes only a single methodological drawback, either in the chemical or biological process. Herein, through the utilization of the bulky steric hindrance of chiral proline derivatives, an integrated laccase and proline as a chemo-enzymatic co-catalyst system is developed. It enables an efficient oxidation/aldol enantioselective sequential reaction to be accomplished, overcoming the mutual deactivation issue. As we present in this study, this one-pot organic transformation, an initial laccase-mediated oxidation of arylbenzyl alcohols and cyclohexanol to form aldehydes and cyclohexanone, followed by a subsequent proline derivative-catalyzed aldol condensation of the in situ generated intermediates, provides various 1,2-diastereoisomeric chiral β-hydroxy ketones with acceptable yields and high enantio-/diastereoselectivities.

中文翻译:

化学酶促氧化/醛醇顺序过程直接将芳基苄醇和环己醇转化为手性 β-羟基羰基

开发用于水性顺序有机转化的酶和有机催化剂的组合具有重要意义,因为它不仅对环境友好,而且在化学或生物过程中仅克服了单一方法学上的缺点。在此,通过利用手性脯氨酸衍生物的庞大空间位阻,开发了一种集成的漆酶和脯氨酸作为化学酶助催化剂系统。它能够实现高效的氧化/醛醇对映选择性顺序反应,克服相互失活问题。正如我们在本研究中所介绍的,这种一锅有机转化,一种初始漆酶介导的芳基苄醇和环己醇氧化形成醛和环己酮,原位产生的中间体,提供了具有可接受的产率和高的各种1,2-非对映异构的手性β羟基酮对映- /非对映选择性。
更新日期:2021-09-17
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