doi:10.1002/chir.23338engGálvez J.A.Badorrey R.Mahía A.Díaz-de-Villegas M.D.Asymmetric synthesis of (1R, 5S)-2-methyl-6, 7-benzomorphan via Aza-Prins reactionART-2021-126167(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.2021http://zaguan.unizar.es/record/11794210.1002/chir.23338http://zaguan.unizar.es/record/117942oai:zaguan.unizar.es:117942Chirality 33, 9 (2021), 543-548by-nc-ndhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/info:eu-repo/semantics/openAccess