<i>N</i>-<i>tert</i>-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles
The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from <i>tert</i>-butanesulfinamide. These imines are versatile chir...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.17.86 |
| _version_ | 1819108199963295744 |
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| author | Joseane A. Mendes Paulo R. R. Costa Miguel Yus Francisco Foubelo Camilla D. Buarque |
| author_facet | Joseane A. Mendes Paulo R. R. Costa Miguel Yus Francisco Foubelo Camilla D. Buarque |
| author_sort | Joseane A. Mendes |
| collection | DOAJ |
| description | The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from <i>tert</i>-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the <i>tert</i>-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral <i>N</i>-<i>tert</i>-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format. |
| first_indexed | 2024-12-22T03:06:09Z |
| format | Article |
| id | doaj.art-2d199ddf733843fa8d625d8ac0c04692 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T03:06:09Z |
| publishDate | 2021-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-2d199ddf733843fa8d625d8ac0c046922022-12-21T18:41:03ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-05-011711096114010.3762/bjoc.17.861860-5397-17-86<i>N</i>-<i>tert</i>-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocyclesJoseane A. Mendes0Paulo R. R. Costa1Miguel Yus2Francisco Foubelo3Camilla D. Buarque4Department of Chemistry, Pontifical Catholic University of Rio de Janeiro Puc-Rio, CEP 22435-900, BrazilLaboratory of Bioorganic Chemistry, Institute of Research of Natural Products, Health Science Center, Federal University of Rio de Janeiro UFRJ, CEP 21941-590, BrazilCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo.99, 03080 Alicante, SpainCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo.99, 03080 Alicante, SpainDepartment of Chemistry, Pontifical Catholic University of Rio de Janeiro Puc-Rio, CEP 22435-900, BrazilThe synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from <i>tert</i>-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the <i>tert</i>-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral <i>N</i>-<i>tert</i>-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.https://doi.org/10.3762/bjoc.17.86asymmetric synthesischiral auxiliarynatural productsnitrogen-containing heterocycles<i>n</i>-<i>tert</i>-butanesulfinyl imines |
| spellingShingle | Joseane A. Mendes Paulo R. R. Costa Miguel Yus Francisco Foubelo Camilla D. Buarque <i>N</i>-<i>tert</i>-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles Beilstein Journal of Organic Chemistry asymmetric synthesis chiral auxiliary natural products nitrogen-containing heterocycles <i>n</i>-<i>tert</i>-butanesulfinyl imines |
| title | <i>N</i>-<i>tert</i>-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles |
| title_full | <i>N</i>-<i>tert</i>-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles |
| title_fullStr | <i>N</i>-<i>tert</i>-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles |
| title_full_unstemmed | <i>N</i>-<i>tert</i>-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles |
| title_short | <i>N</i>-<i>tert</i>-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles |
| title_sort | i n i i tert i butanesulfinyl imines in the asymmetric synthesis of nitrogen containing heterocycles |
| topic | asymmetric synthesis chiral auxiliary natural products nitrogen-containing heterocycles <i>n</i>-<i>tert</i>-butanesulfinyl imines |
| url | https://doi.org/10.3762/bjoc.17.86 |
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