000117942 001__ 117942
000117942 005__ 20230519145510.0
000117942 0247_ $$2doi$$a10.1002/chir.23338
000117942 0248_ $$2sideral$$a126167
000117942 037__ $$aART-2021-126167
000117942 041__ $$aeng
000117942 100__ $$0(orcid)0000-0002-4972-7476$$aGálvez J.A.$$uUniversidad de Zaragoza
000117942 245__ $$aAsymmetric synthesis of (1R, 5S)-2-methyl-6, 7-benzomorphan via Aza-Prins reaction
000117942 260__ $$c2021
000117942 5060_ $$aAccess copy available to the general public$$fUnrestricted
000117942 5203_ $$a(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.
000117942 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc-nd$$uhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
000117942 594__ $$a4.3$$b2021
000117942 590__ $$a2.183$$b2021
000117942 592__ $$a0.397$$b2021
000117942 591__ $$aCHEMISTRY, ORGANIC$$b32 / 57 = 0.561$$c2021$$dQ3$$eT2
000117942 593__ $$aAnalytical Chemistry$$c2021$$dQ3
000117942 591__ $$aCHEMISTRY, ANALYTICAL$$b64 / 87 = 0.736$$c2021$$dQ3$$eT3
000117942 593__ $$aCatalysis$$c2021$$dQ3
000117942 591__ $$aPHARMACOLOGY & PHARMACY$$b222 / 279 = 0.796$$c2021$$dQ4$$eT3
000117942 593__ $$aSpectroscopy$$c2021$$dQ3
000117942 591__ $$aCHEMISTRY, MEDICINAL$$b51 / 63 = 0.81$$c2021$$dQ4$$eT3
000117942 593__ $$aPharmacology$$c2021$$dQ3
000117942 593__ $$aOrganic Chemistry$$c2021$$dQ3
000117942 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000117942 700__ $$0(orcid)0000-0002-5554-3040$$aBadorrey R.$$uUniversidad de Zaragoza
000117942 700__ $$0(orcid)0000-0002-8839-6796$$aMahía A.
000117942 700__ $$0(orcid)0000-0001-9033-8459$$aDíaz-de-Villegas M.D.
000117942 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000117942 773__ $$g33, 9 (2021), 543-548$$pChirality$$tChirality$$x0899-0042
000117942 8564_ $$s946618$$uhttps://zaguan.unizar.es/record/117942/files/texto_completo.pdf$$yVersión publicada
000117942 8564_ $$s2035431$$uhttps://zaguan.unizar.es/record/117942/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000117942 909CO $$ooai:zaguan.unizar.es:117942$$particulos$$pdriver
000117942 951__ $$a2023-05-18-15:11:16
000117942 980__ $$aARTICLE