Asymmetric synthesis of (1R, 5S)-2-methyl-6, 7-benzomorphan via Aza-Prins reaction

Gálvez J.A. (Universidad de Zaragoza) ; Badorrey R. (Universidad de Zaragoza) ; Mahía A. ; Díaz-de-Villegas M.D.

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%. © 2021 The Authors. Chirality published by Wiley Periodicals LLC.

Idioma: Inglés

DOI: 10.1002/chir.23338

Año: 2021

Publicado en: Chirality 33, 9 (2021), 543-548
ISSN: 0899-0042

Factor impacto JCR: 2.183 (2021)

Categ. JCR: CHEMISTRY, ORGANIC rank: 32 / 57 = 0.561 (2021) - Q3 - T2
Categ. JCR: CHEMISTRY, ANALYTICAL rank: 64 / 87 = 0.736 (2021) - Q3 - T3
Categ. JCR: PHARMACOLOGY & PHARMACY rank: 222 / 279 = 0.796 (2021) - Q4 - T3
Categ. JCR: CHEMISTRY, MEDICINAL rank: 51 / 63 = 0.81 (2021) - Q4 - T3

Factor impacto CITESCORE: 4.3 - Chemical Engineering (Q2) - Pharmacology, Toxicology and Pharmaceutics (Q2)

Factor impacto SCIMAGO: 0.397 - Analytical Chemistry (Q3) - Catalysis (Q3) - Spectroscopy (Q3) - Pharmacology (Q3) - Organic Chemistry (Q3)

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)