Intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside

Petra Pádár; Miklós Hornyák; Péter Forgó; Zoltán Kele; Gábor Paragi; Nicola M. Howarth; Lajos Kovács

doi:10.1016/j.tet.2005.04.066

Intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside

Petra Pádár, Miklós Hornyák, Péter Forgó, Zoltán Kele, Gábor Paragi, Nicola M. Howarth, Lajos Kovács

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl a-d-glucopyranoside with 2-furaldehyde has been studied. This cycloaddition was found to afford three 9-oxa-1-azabicyclo[4.2.1] nonane diastereomers in a 3:1:1 ratio [with the principal isomer possessing a (3S,4R,5S,6S,8S) configuration, determined by NMR spectroscopy]. The effects of different Lewis acid catalysts (MgCl₂, ZnCl₂ and BF ₃·OEt₂) on yields and diastereomeric ratios have been examined in detail. The best result (90% yield) was achieved when MgCl ₂ was present (in toluene, 120°C bath temperature, 12 h). The stereoselectivity of the 1,3-dipolar cycloaddition was not significantly altered under the conditions investigated. © 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6816-6823
Number of pages	8
Journal	Tetrahedron
Volume	61
Issue number	28
DOIs	https://doi.org/10.1016/j.tet.2005.04.066
Publication status	Published - 11 Jul 2005

Keywords

1,3-Dipolar cycloaddition
9-Oxa-1-azabicyclo[4.2.1]nonanes
Asymmetric synthesis
Bicyclic 1,2-oxazepanes
Isoxazolidines

Access to Document

10.1016/j.tet.2005.04.066

Cite this

@article{f3856e626cbf4a2dadb1d77b016a4870,

title = "Intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside",

abstract = "The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl a-d-glucopyranoside with 2-furaldehyde has been studied. This cycloaddition was found to afford three 9-oxa-1-azabicyclo[4.2.1] nonane diastereomers in a 3:1:1 ratio [with the principal isomer possessing a (3S,4R,5S,6S,8S) configuration, determined by NMR spectroscopy]. The effects of different Lewis acid catalysts (MgCl2, ZnCl2 and BF 3·OEt2) on yields and diastereomeric ratios have been examined in detail. The best result (90\% yield) was achieved when MgCl 2 was present (in toluene, 120°C bath temperature, 12 h). The stereoselectivity of the 1,3-dipolar cycloaddition was not significantly altered under the conditions investigated. {\textcopyright} 2005 Elsevier Ltd. All rights reserved.",

keywords = "1,3-Dipolar cycloaddition, 9-Oxa-1-azabicyclo[4.2.1]nonanes, Asymmetric synthesis, Bicyclic 1,2-oxazepanes, Isoxazolidines",

author = "Petra P{\'a}d{\'a}r and Mikl{\'o}s Horny{\'a}k and P{\'e}ter Forg{\'o} and Zolt{\'a}n Kele and G{\'a}bor Paragi and Howarth, \{Nicola M.\} and Lajos Kov{\'a}cs",

year = "2005",

month = jul,

day = "11",

doi = "10.1016/j.tet.2005.04.066",

language = "English",

volume = "61",

pages = "6816--6823",

journal = "Tetrahedron",

issn = "1464-5416",

publisher = "Elsevier Ltd",

number = "28",

}

TY - JOUR

T1 - Intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside

AU - Pádár, Petra

AU - Hornyák, Miklós

AU - Forgó, Péter

AU - Kele, Zoltán

AU - Paragi, Gábor

AU - Howarth, Nicola M.

AU - Kovács, Lajos

PY - 2005/7/11

Y1 - 2005/7/11

N2 - The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl a-d-glucopyranoside with 2-furaldehyde has been studied. This cycloaddition was found to afford three 9-oxa-1-azabicyclo[4.2.1] nonane diastereomers in a 3:1:1 ratio [with the principal isomer possessing a (3S,4R,5S,6S,8S) configuration, determined by NMR spectroscopy]. The effects of different Lewis acid catalysts (MgCl2, ZnCl2 and BF 3·OEt2) on yields and diastereomeric ratios have been examined in detail. The best result (90% yield) was achieved when MgCl 2 was present (in toluene, 120°C bath temperature, 12 h). The stereoselectivity of the 1,3-dipolar cycloaddition was not significantly altered under the conditions investigated. © 2005 Elsevier Ltd. All rights reserved.

AB - The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl a-d-glucopyranoside with 2-furaldehyde has been studied. This cycloaddition was found to afford three 9-oxa-1-azabicyclo[4.2.1] nonane diastereomers in a 3:1:1 ratio [with the principal isomer possessing a (3S,4R,5S,6S,8S) configuration, determined by NMR spectroscopy]. The effects of different Lewis acid catalysts (MgCl2, ZnCl2 and BF 3·OEt2) on yields and diastereomeric ratios have been examined in detail. The best result (90% yield) was achieved when MgCl 2 was present (in toluene, 120°C bath temperature, 12 h). The stereoselectivity of the 1,3-dipolar cycloaddition was not significantly altered under the conditions investigated. © 2005 Elsevier Ltd. All rights reserved.

KW - 1,3-Dipolar cycloaddition

KW - 9-Oxa-1-azabicyclo[4.2.1]nonanes

KW - Asymmetric synthesis

KW - Bicyclic 1,2-oxazepanes

KW - Isoxazolidines

UR - https://www.scopus.com/pages/publications/20444433514

U2 - 10.1016/j.tet.2005.04.066

DO - 10.1016/j.tet.2005.04.066

M3 - Article

SN - 1464-5416

VL - 61

SP - 6816

EP - 6823

JO - Tetrahedron

JF - Tetrahedron

IS - 28

ER -

Intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this