Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3461-3464

  Xu, Zhenrong ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030919677     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00656-4     Document Type: Article

References (23)

1. For reviews on [3+2] cycloadditions, see: Little, R. D.; Chan, D. M. T. [3+2] cycloadditions: Thermal Cycloadditions. Transition Metal Mediated Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991; vol. 5, pp 239-314.
2. For some recent examples, see: (a) Ghera, E.; Yechezkel, T.; Hassner, A. J. Org. Chem. 1996, 61, 4959-4966.
3. (b) Walters, M. A.; Arcand, H. R. J. Org. Chem. 1996, 61, 1478-1486.
4. (c) Hojo, M.; Ishibashi, N.; Hosomi, A. Synlett 1996, 234-236.
5. (d) Wittland, C.; Arend, M.; Risch, N. Synthesis 1996, 367-371.
6. (e) A non-concerted process, Lu, Y.-Q.; Li, C.-J. Tetrahedron Lett. 1996, 37, 471-474.
7. Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908.
8. For recent synthesis of N-tosylimines, see: (a) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366-7368.
9. (b) Love, B. E.; Raje, P. S.; Williams II, T. C. Synlett 1994, 493-494.
10. (c) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777-4780.
11. (d) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468-6470.
12. (e) Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561-5568.
13. For the formation of five-membered rings, see: (a) Jiang, S.; Chen, T.; Turos, E. Organometallics 1995, 14, 4710-4720.
14. (b) Chen, T.; Jiang, S.; Turos, E. Tetrahedron Lett. 1994, 35, 8325-8328.
15. (c) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636-6645.
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17. (e) Saigo, K.; Shimada, S.; Hasegawa, M. Chem. Lett. 1990, 905-908.
18. 4S (357.44): C, 63.85; H, 5.36; N, 3.92. Found: C, 63.59; H, 5.18; N, 3.65.
19. If a trapping reagent is less active than 1, the self cycloaddition product of 1 is formed. See ref 3.
20. β bond, the delocalized structure 5′ was formed, which results in the formation of 4. For a similar result, see: Zhang, C.; Lu, X. Synleu 1995, 645-646.
21. 2Me, 10.65), 115 (32.85), 114 (8.08) and 89 (5.97).
22. Padwa, A.; Smolanoff, J.; Tremper, A. J. Am Chem. Soc. 1975, 97, 4682-4691.
23. The electron rich aryl groups are readily cleaved oxidatively by DDQ. See: Nakajima, N.; Abe, R.; Yonemitsu, O. Chem. Pharm. Bull. 1988, 36, 4244-4247.