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http://hdl.handle.net/10397/94269
| Title: | Diastereoselective bidirectional C(sp3)−H bond functionalization of piperazine compounds | Authors: | Zhou, XL Yeung, CT Kwok Chan, WT Law, GL |
Issue Date: | Feb-2022 | Source: | Advanced synthesis & catalysis, 15 Feb. 2022, v. 364, no. 4, p. 732-737 | Abstract: | A highly diastereoselective bidirectional C(sp3)−H bond functionalization of piperazine compounds, triggered by a Lewis acid catalyzed sequential hydride shift/cyclization process, is reported. Catalysts and ligands are key factors that control the diastereoselectivity of the reaction. The reaction affords the product with good yield and high diastereoselectivity. Detailed investigation of the reaction mechanism reveals that the energy barrier between the cis products and trans products results in the diastereoselectivity of the reaction. The trans products, which have higher energy and which are generated from the cis products, act as intermediate products. | Keywords: | Bidirectional C(sp3)−H functionalization Lewis acid catalysis Sc(OTf)3 Trans/cis diastereoselectivity |
Publisher: | Wiley-VCH | Journal: | Advanced synthesis & catalysis | ISSN: | 1615-4150 | EISSN: | 1615-4169 | DOI: | 10.1002/adsc.202101187 | Rights: | © 2022 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited. The following publication Zhou, X. L., Yeung, C. T., Kwok Chan, W. T., & Law, G. L. (2022). Diastereoselective Bidirectional C (sp3)− H Bond Functionalization of Piperazine Compounds. Advanced Synthesis & Catalysis, 364(4), 732-737 is available at https://doi.org/10.1002/adsc.202101187 |
| Appears in Collections: | Journal/Magazine Article |
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| File | Description | Size | Format | |
|---|---|---|---|---|
| Zhou_C(sp3)−H_Piperazine_Compounds.pdf | 6.26 MB | Adobe PDF | View/Open |
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