Ghent University Academic Bibliography

Advanced

Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates

Diederica Claeys UGent, Christian Stevens UGent, Bart Roman UGent, Pieter Van de Caveye UGent, Michel Waroquier UGent and Veronique Van Speybroeck UGent (2010) ORGANIC & BIOMOLECULAR CHEMISTRY. 8(16). p.3644-3654
abstract
Phosphonylated azaheterocycles are an important class of compounds with high biological potential as conformationally restricted bioisosteres of amino acids. Therefore, it is of interest to synthesize conformationally constrained amino phosphonates. We wanted to investigate possible routes via ring opening of alpha-amino phosphonates with an oxanorbornene skeleton, as these can be synthesized with high stereoselectivity. This was achieved using different Lewis acids, leading to a range of products. The reaction with TiCl4 and FeCl3 was modelled at a DFT level of theory to get insight in the pathways towards the corresponding products. To ease the work up, the Fe(III) catalyst was coated on montmorillonite clay, but this accelerated aromatization after ring opening. Quenching the FeCl3 catalyzed reaction mixture on celite caused complete aromatization.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
IMDAF CYCLOADDITION, DENSITY-FUNCTIONAL THEORY, MONTMORILLONITE K10, AMINOPHOSPHONIC ACIDS, BIOLOGICAL-ACTIVITY, MOLECULAR CALCULATIONS, AB-INITIO, DIELS-ALDER REACTIONS, OXABICYCLIC ALKENES, EFFECTIVE CORE POTENTIALS
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
8
issue
16
pages
3644 - 3654
Web of Science type
Article
Web of Science id
000280527500010
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.451 (2010)
JCR rank
12/56 (2010)
JCR quartile
1 (2010)
ISSN
1477-0520
DOI
10.1039/c002926b
project
HPC-UGent: the central High Performance Computing infrastructure of Ghent University
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1027212
handle
http://hdl.handle.net/1854/LU-1027212
date created
2010-08-23 09:33:26
date last changed
2016-12-19 15:46:24
@article{1027212,
  abstract     = {Phosphonylated azaheterocycles are an important class of compounds with high biological potential as conformationally restricted bioisosteres of amino acids. Therefore, it is of interest to synthesize conformationally constrained amino phosphonates. We wanted to investigate possible routes via ring opening of alpha-amino phosphonates with an oxanorbornene skeleton, as these can be synthesized with high stereoselectivity. This was achieved using different Lewis acids, leading to a range of products. The reaction with TiCl4 and FeCl3 was modelled at a DFT level of theory to get insight in the pathways towards the corresponding products. To ease the work up, the Fe(III) catalyst was coated on montmorillonite clay, but this accelerated aromatization after ring opening. Quenching the FeCl3 catalyzed reaction mixture on celite caused complete aromatization.},
  author       = {Claeys, Diederica and Stevens, Christian and Roman, Bart and Van de Caveye, Pieter and Waroquier, Michel and Van Speybroeck, Veronique},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {IMDAF CYCLOADDITION,DENSITY-FUNCTIONAL THEORY,MONTMORILLONITE K10,AMINOPHOSPHONIC ACIDS,BIOLOGICAL-ACTIVITY,MOLECULAR CALCULATIONS,AB-INITIO,DIELS-ALDER REACTIONS,OXABICYCLIC ALKENES,EFFECTIVE CORE POTENTIALS},
  language     = {eng},
  number       = {16},
  pages        = {3644--3654},
  title        = {Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates},
  url          = {http://dx.doi.org/10.1039/c002926b},
  volume       = {8},
  year         = {2010},
}

Chicago
Claeys, Diederica, Christian Stevens, Bart Roman, Pieter Van de Caveye, Michel Waroquier, and Veronique Van Speybroeck. 2010. “Experimental and Computational Study of the Ring Opening of Tricyclic Oxanorbornenes to Polyhydro Isoindole Phosphonates.” Organic & Biomolecular Chemistry 8 (16): 3644–3654.
APA
Claeys, Diederica, Stevens, C., Roman, B., Van de Caveye, P., Waroquier, M., & Van Speybroeck, V. (2010). Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates. ORGANIC & BIOMOLECULAR CHEMISTRY, 8(16), 3644–3654.
Vancouver
1.
Claeys D, Stevens C, Roman B, Van de Caveye P, Waroquier M, Van Speybroeck V. Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates. ORGANIC & BIOMOLECULAR CHEMISTRY. 2010;8(16):3644–54.
MLA
Claeys, Diederica, Christian Stevens, Bart Roman, et al. “Experimental and Computational Study of the Ring Opening of Tricyclic Oxanorbornenes to Polyhydro Isoindole Phosphonates.” ORGANIC & BIOMOLECULAR CHEMISTRY 8.16 (2010): 3644–3654. Print.