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

Tetrahedron

Volumn 61, Issue 28, 2005, Pages 6816-6823

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

^a UNIVERSITY OF SZEGED   (Hungary)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

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

Indexed keywords

GLUCOPYRANOSIDE; ISOXAZOLIDINE DERIVATIVE; LEWIS ACID; NITRONE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLOADDITION; DIASTEREOISOMER; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE MEASUREMENT;

EID: 20444433514     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.066     Document Type: Article

References (21)

1. M. Egholm, O. Buchardt, L. Christensen, C. Behrens, S.M. Freier, D.A. Driver, R.H. Berg, S.K. Kim, B. Norden, and P.E. Nielsen Nature 365 1993 566 568
2. P.E. Nielsen M. Egholm Peptide Nucleic Acids: Protocols and Applications 1999 Horizon Scientific Wymondham, UK
3. K.V. Gothelf S. Kobayashi K.A. Jorgensen Cycloaddition Reactions in Organic Synthesis 2002 Wiley-VCH Weinheim 211 247
4. K.V. Gothelf, and K.A. Jorgensen Acta Chem. Scand. 50 1996 652 660
5. J. Tanaka, and S. Kanemasa Tetrahedron 57 2001 899 905
6. P. Merino, S. Anoro, F.L. Merchan, and T. Tejero Molecules 5 2000 132 152
7. P. Merino, S. Anoro, E. Cerrada, M. Laguna, A. Moreno, and T. Tejero Molecules 6 2001 208 220
8. P. Merino, T. Tejero, M. Laguna, A. Moreno, E. Cerrada, and J.A. Lopez Org. Biomol. Chem. 1 2003 2336 2342
9. P.J. Garegg, and B. Samuelsson J. Chem. Soc., Perkin Trans. 1 1980 2866 2869
10. B. Bernet, and A. Vasella Helv. Chim. Acta 62 1979 1990 2016
11. P.R. Skaanderup, L. Hyldtoft, and R. Madsen Monatsh. Chem. 133 2002 467 472
12. M. Kleban, U. Kautz, J. Greul, P. Hilgers, R. Kugler, H.Q. Dong, and V. Jäger Synthesis 2000 1027 1033
13. E. Erdik Tetrahedron 43 1987 2203 2212
14. R.D. Smith, and H.E. Simmons Organic Synthesis Coll. Vol. 1973 pp 855-858
15. R.D. Rieke, P.T.J. Li, T.P. Burns, and S.T. Uhm J. Org. Chem. 46 1981 4323 4324
16. R.D. Rieke Aldrichimica Acta 33 2000 52 60
17. A. Vasella Helv. Chim. Acta 60 1977 426 446
18. J.K. Gallos, A.E. Koumbis, V.P. Xiraphaki, C.C. Dellios, and E. Coutouli-Argyropoulou Tetrahedron 55 1999 15167 15180
19. Tripos Inc. Sybyl 6.9. 1699 South Hanley Rd, St. Louis, Missouri 63144, USA. 2002.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, Ö.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komáromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A., Gaussian 03, Revision A.1. Gaussian, Inc., Pittsburgh, PA. 2003.
21. W.L.F. Armarego, and C.L.L. Chai Purification of Laboratory Chemicals 5th ed. 2003 Elsevier Amsterdam