Article

Full Access

Synthesis of 5-fluoroalkyl lsoxazolidines via 1,3-dipolar cycloaddition of ethyl 2-hydropolyfluoroalk-2-enoates with nitrones^†

Corresponding Author

Jin-Tao Liu

[email protected]

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Fax: 021-64166128Search for more papers by this author

Qi-Hui Jin,

Qi-Hui Jin

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Search for more papers by this author

He-Jun Lü,

He-Jun Lü

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Search for more papers by this author

Wei-Yuan Huang,

Wei-Yuan Huang

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Search for more papers by this author

Jin-Tao Liu,

Corresponding Author

Jin-Tao Liu

[email protected]

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Fax: 021-64166128Search for more papers by this author

Qi-Hui Jin,

Qi-Hui Jin

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Search for more papers by this author

He-Jun Lü,

He-Jun Lü

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Search for more papers by this author

Wei-Yuan Huang,

Wei-Yuan Huang

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Search for more papers by this author

First published: 26 August 2010

https://doi.org/10.1002/cjoc.20040220914

Citations: 3

^†

Dedicated to Professor Chengye Yuan on the occasion of his 80th birthday.

About

PDF

Tools

Share a link

Email
Wechat
Bluesky

Abstract

1,3-Dipolar cycloaddition reactions of ethyl 2-hydropolyfluoroalk-2-enoates (1) with some nitrones were described. The reaction of 3,4-dihydroisoquinoline N-oxide (2) with 1 took place readily in methylene chloride at room temperature to give the corresponding 5-fluoroalkylisoxazolidines regioselectively as a mixture of two diastereoisomers (trans and cis) in high yields, while longer reaction time and higher temperature were needed in the case of non-cyclic nitrones. Under similar conditions the reaction of quinoline N-oxide (14) with 1 did not give the expected adducts and a ring-opening product was obtained.

References

1(a) Silvester, J. M. Aldrichimca Acta 1991, 24, 31.
CAS Google Scholar
(b) Filler, R.; Kobayashi, Y. Biomedical Aspects of Fluorine Chemisrty, Elsevier, New York, 1992.
Google Scholar
(c) Welch, J. T. Tetrahedron 1987, 43, 3123.
10.1016/S0040-4020(01)90286-8
CAS Web of Science® Google Scholar
2(a) Confalone, P. N.; Huie, E. M. Org. React. 1998, 36, 1.
Google Scholar
(b) Tufariello, J. J. 1, 3-Dipolar Cycloaddition Chemistry, Vol. 12, Ed.: A. Padwa, John Wiley and Sons, New York, 1984, p. 83.
Google Scholar
(c) Torsell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, Ed.: H. Feuer, VCH Publisher, New York, 1988.
Google Scholar
(d) Padwa, A. Comprehensive Organic Synthesis, Vol. 4, Eds.: B. M. Trost; I. Fleming, Pergamon Press, Oxford, 1991, p. 1069.
10.1016/B978-0-08-052349-1.00116-5
Google Scholar
3(a) Zhang, X.-C.; Huang, W.-Y. J. Fluorine Chem. 1998, 92, 13.
10.1016/S0022-1139(98)00241-3
CAS Web of Science® Google Scholar
(b) Zhang, X.-C.; Huang, W.-Y. J. Fluorine Chem. 1998, 87, 57.
10.1016/S0022-1139(97)00118-8
CAS Web of Science® Google Scholar
(c) Zhang, X.-C.; Huang, W.-Y. Tetrahedron Lett. 1997, 27, 4827.
10.1016/S0040-4039(97)01021-6
PubMed Web of Science® Google Scholar
(d) Zhang, X.-C.; Huang, W.-Y. Tetrahedron 1998, 54, 12465.
10.1016/S0040-4020(98)00728-5
CAS Web of Science® Google Scholar
4 Liu, J.-T.; Jin, Q.-H.; Lü, H.-J.; Huang, W.-Y. Tetrahedron Lett. 2001, 42, 5937.
10.1016/S0040-4039(01)01162-5
CAS Web of Science® Google Scholar
5 Huang, W.-Y.; Lü, L.; Zhang, Y.-F. Chin. J. Chem. 1990, 281.
Google Scholar
6(a) Lunn, G.; Sansone, E. B. J. Org. Chem. 1986, 51, 513.
10.1021/jo00354a021
CAS Web of Science® Google Scholar
(b) Murahashi, S. I.; Shiota, T. Tetruhedron Lett. 1987, 28, 2383.
10.1016/S0040-4039(00)96130-6
CAS Web of Science® Google Scholar
(c) Coperet, C.; Adolfsson, H.; Khuong, T. V.; Yudin, A. K.; Sharpless, K. B. J. Org. Chem. 1998, 63, 1740.
10.1021/jo9723467
CAS Web of Science® Google Scholar
(d) Chan, K. S.; Yeung, M. L.; Chan, W.-K.; Wang, R.-J.; Mak, T. C. W. J. Org. Chem. 1995, 60, 1741.
10.1021/jo00111a036
CAS Web of Science® Google Scholar
7 X-ray data for compound 3a: C₁₇H₁₅C1F₇NO₃, M=449.75, monoclinic, crystal dimensions 0.2 mm × 0.2 mm × 0.3 mm, a=0.9926(2) nm, b=1.0660(2) nrn, c=1.8251(3) nm, V=1.8788(6) nm³, D,= 1.590 g/cm³, 2=4, F₀₀₀ = 912.00, μ(Mo Kα)=2.89 cm⁻¹. Data were measured at 293 K on a Bruker SMART CCD diffractometer with graphite mono-chromated Mo Kα radiation.
Google Scholar
8 Iwao, M.; Kuraishi, T. J. Heterocycl. Chem. 1978, 15, 1425.
10.1002/jhet.5570150836
CAS Web of Science® Google Scholar

Citing Literature

Volume22, Issue9

September 2004

Pages 945-949

Synthesis of 5-fluoroalkyl lsoxazolidines via 1,3-dipolar cycloaddition of ethyl 2-hydropolyfluoroalk-2-enoates with nitrones^†

Abstract

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Synthesis of 5-fluoroalkyl lsoxazolidines via 1,3-dipolar cycloaddition of ethyl 2-hydropolyfluoroalk-2-enoates with nitrones†

Abstract

References

Citing Literature

References

Related

Information

Synthesis of 5-fluoroalkyl lsoxazolidines via 1,3-dipolar cycloaddition of ethyl 2-hydropolyfluoroalk-2-enoates with nitrones^†