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Título: | Asymmetric synthesis of (1R,5S)-2-methyl-6,7-benzomorphanvia Aza-Prins reaction |
Autor: | Gálvez, José A. CSIC ORCID; Badorrey, Ramón CSIC ORCID; Mahía Moros, Alejandro CSIC; Díaz de Villegas, María D. CSIC ORCID | Fecha de publicación: | 19-jul-2021 | Editor: | John Wiley & Sons | Citación: | Chirality 33(9): 543–548 (2021) | Resumen: | (1R,5S)-2-Methyl-6,7-benzomorphan has been synthesised from (R)-(benzyloxy)(phenyl)acetaldehyde. On a 2-mmol scale Bi (OTf)3 promoted Aza-Prins reaction with N-tosylhomoallylamine afforded an 88/12 mixture of 6-oxa-2-azabicyclo[3.2.1]octanes. Major diastereoisomer was converted to enantiomerically pure (2S,4S)-2-benzyl-1- methylpiperidin-4-ol via a high-yielding sequence hydrogenolysis/N-detosylation/N-methylation. Acid-catalysed intramolecular Friedel−Crafts cyclisation of the piperidinol afforded (1R,5S)-2-methyl-6,7-benzomorphan in five steps with a yield of 25%. | Versión del editor: | https://doi.org/10.1002/chir.23338 | URI: | http://hdl.handle.net/10261/253739 | DOI: | 10.1002/chir.23338 | ISSN: | 0899-0042 | E-ISSN: | 1520-636X |
Aparece en las colecciones: | (IQF) Artículos (ISQCH) Artículos |
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Asymmetric synthesis.pdf | Artículo principal | 924,28 kB | Adobe PDF | Visualizar/Abrir |
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