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)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. If you remix, transform, or build upon the material, you may not distribute the modified material.
Exportado de SIDERAL (2023-05-18-15:11:16)
Visitas y descargas
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)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. If you remix, transform, or build upon the material, you may not distribute the modified material. Exportado de SIDERAL (2023-05-18-15:11:16)
Permalink:
Visitas y descargas
Este artículo se encuentra en las siguientes colecciones:
Articles > Artículos por área > Química Orgánica
Record created 2022-08-17, last modified 2023-05-19