117942 20230519145510.0 doi 10.1002/chir.23338 sideral 126167 ART-2021-126167 eng Gálvez J.A. Universidad de Zaragoza (orcid)0000-0002-4972-7476 Asymmetric synthesis of (1R, 5S)-2-methyl-6, 7-benzomorphan via Aza-Prins reaction 2021 Access copy available to the general public Unrestricted (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%. © 2021 The Authors. Chirality published by Wiley Periodicals LLC. info:eu-repo/semantics/openAccess by-nc-nd http://creativecommons.org/licenses/by-nc-nd/3.0/es/ 2.183 2021 CHEMISTRY, ORGANIC 32 / 57 = 0.561 2021 Q3 T2 CHEMISTRY, ANALYTICAL 64 / 87 = 0.736 2021 Q3 T3 PHARMACOLOGY & PHARMACY 222 / 279 = 0.796 2021 Q4 T3 CHEMISTRY, MEDICINAL 51 / 63 = 0.81 2021 Q4 T3 0.397 2021 Analytical Chemistry 2021 Q3 Catalysis 2021 Q3 Spectroscopy 2021 Q3 Pharmacology 2021 Q3 Organic Chemistry 2021 Q3 4.3 2021 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Badorrey R. Universidad de Zaragoza (orcid)0000-0002-5554-3040 Mahía A. (orcid)0000-0002-8839-6796 Díaz-de-Villegas M.D. (orcid)0000-0001-9033-8459 2013 765 Universidad de Zaragoza Dpto. Química Orgánica Área Química Orgánica 33, 9 (2021), 543-548 Chirality Chirality 0899-0042 946618 http://zaguan.unizar.es/record/117942/files/texto_completo.pdf Versión publicada 2035431 http://zaguan.unizar.es/record/117942/files/texto_completo.jpg?subformat=icon icon Versión publicada oai:zaguan.unizar.es:117942 articulos driver 2023-05-18-15:11:16 ARTICLE