Stereoselective Chemoenzymatic Synthesis of Enantiopure 1‐(Heteroaryl)ethanamines by Lipase‐Catalysed Kinetic Resolutions
Abstract The efficient chemical synthesis and enzymatic kinetic resolution of a family of 1‐(heteroaryl)ethanamines have been performed with lipases responsible for the preparation of nitrogenated compounds in high optical purity. Thus, Candida antarctica lipase type B has been identified as an exce...
| Published in: | European Journal of Organic Chemistry |
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| Main Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
2009
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| Subjects: | |
| Online Access: | http://dx.doi.org/10.1002/ejoc.200900150 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.200900150 http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.200900150/fullpdf |
| Summary: | Abstract The efficient chemical synthesis and enzymatic kinetic resolution of a family of 1‐(heteroaryl)ethanamines have been performed with lipases responsible for the preparation of nitrogenated compounds in high optical purity. Thus, Candida antarctica lipase type B has been identified as an excellent biocatalyst for the stereoselective production of the corresponding enantiomerically enriched ( R )‐acetamides and ( S )‐amines. A similar effect of the heteroatom in the cyclic ring has been observed in terms of reactivity and enantioselectivity, with benzoxazole, benzothiazole and benzimidazole derivatives being obtained with excellent enantiopurities after one day of reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) |
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