N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles
| Autor: | Camilla D. Buarque, Joseane A. Mendes, Miguel Yus, Paulo R. R. Costa, Francisco Foubelo |
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| Přispěvatelé: | Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Síntesis Asimétrica (SINTAS) |
| Rok vydání: | 2021 |
| Předmět: |
Nitrogen-containing heterocycles
natural products Science asymmetric synthesis Imine chemistry.chemical_element N-tert-butanesulfinyl imines Review Reaction intermediate Chiral auxiliary chemistry.chemical_compound QD241-441 chiral auxiliary Group 2 organometallic chemistry Natural products Nucleophilic addition Organic Chemistry Enantioselective synthesis nitrogen-containing heterocycles Asymmetric synthesis Nitrogen Combinatorial chemistry Chemistry Química Orgánica chemistry Nitrogen atom n-tert-butanesulfinyl imines |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 1096-1140 (2021) Beilstein Journal of Organic Chemistry RUA. Repositorio Institucional de la Universidad de Alicante Universidad de Alicante (UA) |
| ISSN: | 1860-5397 |
| Popis: | 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 tert-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 tert-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 N-tert-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. We thank the continuous financial support from the Spanish Ministerio de Economía y Competitividad (MINECO; project CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P), Ministerio de Ciencia, Innovación y Universidades (RED2018-102387-T, PID2019-107268GB-100), FEDER, the Generalitat Valenciana (PROMETEOII/2014/017), and the University of Alicante (VIGROB-068). We are also grateful for the financial support from Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES). |
| Databáze: | OpenAIRE |
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