Tandem inter [4+2]/intra [3+2] cycloadditions. 8. Cycloadditions with unactivated dipolarophiles

Tetrahedron

Volumn 52, Issue 35, 1996, Pages 11579-11600

  Denmark, Scott E ^a   Senanayake, C B W ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 OXAZINE DERIVATIVE; POLYCYCLIC HYDROCARBON; PYRROLE DERIVATIVE;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030603138     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00642-4     Document Type: Article

References (22)

1. (1) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137-165.
2. (2) Sauer, J.; Sustmann, R.; Angew. Chem., Int. Ed. Engl. 1980, 19, 779-807.
3. (3) (a) Takaeuchi, Y.; Furusaki, F. In Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J., Ed.; Academic, New York, 1977, Vol. 21. p 207-251.
4. (b) Shipchandler, M. T. Synthesis, 1979, 666-686.
5. (c) Tartakovskii, V. A. Izv. Akad. Nauk. SSSR, Ser. Chim. 1984, 33, 147-155 (Engl. Transl.).
6. (d) Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH, Weinheim, 1988.
7. (e) Breuer, E.; Aurich, H. G.; Nielsen, A. Nitrones, Nitronates, and Nitroxides, Wiley, New York, 1990, p 105-111.
8. (f) Döpp, H.; Döpp, D. In Methoden der Organischen Chemie (Houben-Weyl), Klamann, D.; Hagemann, H., Ed.; Georg Thieme, Stuttgart, 1990, 4th ed, Vol. E14b/1, p 880-960.
9. (4) (a) Tohda, Y.; Yamawaki, N.; Matsui, H.; Kawashima, T.; Ariga, M.; Mori, Y. Bull. Chem. Soc. Jpn. 1988, 61, 461-465.
10. (b) Tohda, Y.; Tani, K.; Yamawaki, N.; Ariga, M.; Nishiwaki, N.; Kotani, K.; Matsumura, E. Bull. Chem. Soc. Jpn. 1993, 66, 1222-1228.
11. (c) Papchikhin, A.; Agback, P.; Plavec, J.; Chattopadhyaya, J. J. Org. Chem, 1993, 58, 2874-2879.
12. (5) Dehaen, W.; Hassner, A. Tetrahedron Lett. 1990, 31, 743-746.
13. (6) (a) Kharasch, M. S.; Fuchs, C. F. J. Org. Chem. 1944, 9, 359-372.
14. (b) Cekovic, Z.; Green, M. M. J. Am. Chem. Soc. 1974, 96, 3000-3002.
15. (c) Coates, R. M.; Ley, D. A.; Cavender, P. L. J. Org. Chem. 1978, 43, 4915-4922.
16. (7) Denmark, S. E.; Moon, Y.-C.; Senanayake, C. B. W. J. Am. Chem. Soc. 1990, 112, 311-315.
17. (8) Breitmaier, E.; Voelter, W. "Carbon-13 NMR Spectroscopy, Third Edition"; VCH: Weinheim, 1990; pp 380-400.
18. (9) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A. Ed.; Wiley, 1984, Vol. 1-2.
19. (10) For a discussion of the mechanism of this process see: Denmark S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672-5680.
20. (11) Claus, R. E.; Schreiber, S. L. Org. Synth. 1985, 64, 150-156.
21. (12) (a) Schlosser, M.; Christmann, K. F. Angew. Chem., Int. Ed. Engl. 1964, 3, 636-637.
22. (b) Pritchard, J. G.; Nelson, H. M. J. Phys. Chem. 1960, 64, 795-801.