Non-cycloaddition approach to regioselective synthesis of isoxazolidines

Synlett

Volumn , Issue 9, 1998, Pages 979-980

  Niu, Deqiang ^a   Zhao, Hongjuan ^a   Doshi, Amish ^a   Zhao, Kang ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345715710     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1840     Document Type: Article

References (30)

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4. (d) Pan, S.; Amankulor, G.; Zhao, K. Tetrahedron, 1998, 54, 6587.
5. (e) The Michael addition of hydroxylamine derivatives to tri-substituted enoates gives only the trans products 7 and the results will be reported shortly, see: Niu, D.; Zhao, K. manuscript in preparation.
6. Pan, S.; Wang, G.; Zhao, K. submitted for publication.
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15. 13C-NMR and NOESY spectra. The chemical shifts of two 4-gem hydrogens are broadly separated (> 0.5 ppm) in the cis isomer while those hydrogens in the trans isomer have the same chemical shifts. This NMR pattern was also used for the characterization of other related products 9. See also references 1b-c.
16. For selected reviews, see: (a) Kozikowski, A. P. Acc. Chem Res. 1984, 17, 410.
17. (b) Caramella, P.; Grünanger, P. 1,3-Dipolar Cycloaddition Chemistry, ed. Padwa, A. Wiley, Chichester, 1984; Vol. 1, p 291.
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22. A few non-dipolar addition methods have also been reported recently, see: (a) Malamas, M.; Palka, C. J. Heterocyclic Chem. 1996, 33, 475.
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24. (c) Socha, D.; Jurczak, M.; Chmielewski, M. Tetrahedron 1997, 53, 739.
25. It can be assumed that the trans product 9e results from the oxonium intermediate shown below.
26. 3) cis 9a δ 7.39-7.30 (m, 5H), 5.96-5.76 (m, 1H), 5.17-5.06 (m, 2H), 4.37-4.23 (m, 1H), 3.63 (t, 1H, J = 8.25 Hz), 2.83-2.69 (m, 1H), 2.66-2.52 (m, 1H), 2.61 (s, 3H), 2.43-2.29 (m, 1H), 2.15-2.01 (m, 1H); trans 9a δ 7.40-7.29 (m, 5H), 5.96-5.75 (m, 1H), 5.20-5.08 (m, 2H), 4.40-4.26 (m, 1H), 3.53-3.45 (m, 1H), 2.59 (s, 3H), 2.50-2.27 (m, 4H); 9b δ 5.92-5.69 (m, 1H), 5.14-5.02 (m, 2H), 2.64 (s, 3H), 2.56-2.18 (m, 2H), 2.04-1.92 (m, 1H), 1.72-1.56 (m, 1H), 1.16 (d, J = 6.22 Hz) and 1.14 (d, J = 6.18 Hz) (3H, 2 isomers); 9e δ 5.90-5.70 (m, 1H), 5.16-5.02 (m, 2H), 4.08-4.01 (dd, 2H, J = 8.58, 6.68 Hz), 3.80-3.66 (m, 1H), 3.38-3.23 (m, 1H), 2.62 (s, 3H), 2.50-2.18 (m, 3H), 1.75-1.60 (m, 1H); 9g δ 5.96-5.74 (m, 1H), 5.17-5.03 (m, 2H), 4.15-4.01 and 3.73-3.63 (m, 1H, 2 isomers), 2.65 (s, 3H), 2.40-1.82 (m, 4H), 1.15-0.96 (m, 6H, 2 isomers); 9h δ 7.39-7.26 (m, 5H), 6.03-5.80 (m, 1H), 5.20-5.06 (m, 2H), 4.39-4.28 (cis) and 3.90-3.81 (trans) (m, 1H), 3.13 (d, J = 9.44, trans) and 2.99 (d, J = 8.42, cis) (1H), 2.59 (trans) and 2.58 (cis) (s, 3H), 2.69-2.22 (m, 3H), 1.03 (d, J = 6.72, trans) and 1.00 (d, J = 7.08, cis) (3H).
27. (a) Tsuge, H.; Okano, T.; Eguchi, S. J. Chem. Soc., Perkin Trans. 1 1995, 2761.
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