Intramolecular 4+3 Cycloadditions. Further Studies of (Trimethylsilyl)methyl Allylic Sulfones

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 6051-6055

  Harmata, Michael ^a   Herron, Barry F ^a   Kahraman, Mehmet ^a   Barnes, Charles L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000414224     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970511c     Document Type: Article

References (21)

1. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
2. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
3. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
4. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
5. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
6. For a review of intramolecular 4 + 3 cycloadditions, see: (a) Harmata, M. Tetrahedron 1997, 53, 6235. (b) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1997; Vol. 4, pp 41-86.
7. For a review of intramolecular 4 + 3 cycloadditions, see: (a) Harmata, M. Tetrahedron 1997, 53, 6235. (b) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1997; Vol. 4, pp 41-86.
8. Harmata, M.; Herron B. F. J. Org. Chem. 1993, 58, 7393.
9. Harmata, M.; Herron, B. F. Synthesis 1993, 202.
10. Giguere,R. J.; Duncan, S. M.; Bean, J. M.; Purvis, L. Tetrahedron Lett. 1988, 29, 6071.
11. The relative ratios were based on capilliary GC analysis of the crude reaction mixture.
12. The ring fusion stereochemistry of this compound had been established by other means. See reference 5.
13. It is presumed that the angular hydrogen of 6d occurs as part of a two-proton multuplet at 2.60-2.41 ppm.
14. Harmata, M.; Gamlath, C. B.; Barnes, C. L.; Jones, D. E. J. Org. Chem. 1995, 60, 5077.
15. The author has deposited atomic coordinates for this structure with the Cambridge Cry stall ographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2, 1EZ, UK.
16. Presumably, the trimethylaluminum used to effect heterolysis of the phenylsulfonyl group also serves as the source of the methyl group present in the dihydrofuran ring of 11b.
17. The preference of 22a over 22b can be viewed as an avoidance of 1,3-allylic strain. See: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
18. We are unaware of any studies involving the coordination of furans to Lewis acids and the effect such coordination might have on the course of chemical reactions. However, the absence of metal binding by calixfurans has been noted. See: de Sousa Healy, M.; Rest, A. J. J. Chem. Soc., Perkin Trans. 1 1985, 973.
19. Stereocontrol via furan coordination of a metal cation in an intermolecular 4 + 3 cycloaddition has been proposed. See: Lautens, M.; Aspiotis, R.; Colucci, J. J. Am. Chem. Soc. 1996, 118, 10930.
20. For general experimental information, see reference 3.
21. The synthesis of the alkyl halide needed for the synthesis of 13 and 15 has been described. See: Harmata, M.; Gamlath, C. B.; Barnes, C. L.; Jones, D. E. J. Org. Chem. 1995, 60, 5077.