Synthesis of medium-sized rings, spiro-annulated oxazacycles and 1- amino-3-siloxy dienes based on regioselective reactions of ambident dianions

Synlett

Volumn , Issue 1, 1999, Pages 135-137

  Langer, Peter ^a   Döring, Manfred ^b   Seyferth, Dietmar ^c  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

1 amino 3 siloxy dienes; Ambident dianions; Medium sized rings; Regioselectivity; Spiro compounds

Indexed keywords

ALKADIENE; ANION;

ARTICLE; CYCLIZATION; ISOMERISM; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0039107060     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2537     Document Type: Article

References (34)

1. Regioselective Reactions of Ambident Dianions, part 6. For part 5, see reference 4(f).
2. th ed., vol. E19d, 1993, 448. See also: Thompson, C. M.; Green, D. Tetrahedron 1991, 47, 4223.
3. th ed., vol. E19d, 1993, 448. See also: Thompson, C. M.; Green, D. Tetrahedron 1991, 47, 4223.
4. (a) Seebach, D.; Pohmakotr, M. Tetrahedron 1981, 37, 4047.
5. (b) Vollhardt, J.; Gais, H.-J.; Lukas, L. Angew. Chem., Int. Ed. Engl. 1985, 24, 608.
6. (c) Maercker, A.; Theis, M. Topics Curr. Chem. 1987, 138, 1.
7. (d) Maercker, A.; Groos, A. Angew. Chem. 1996, 108, 216; Angew. Chem., Int. Ed. Engl. 1996, 35, 210.
8. (d) Maercker, A.; Groos, A. Angew. Chem. 1996, 108, 216; Angew. Chem., Int. Ed. Engl. 1996, 35, 210.
9. (e) Katritzky, A. R.; Fali, C. N.; Li, J. J. Org. Chem. 1997, 62, 4148.
10. For recent work from our laboratory on cyclization reactions of ambident dianions, see: (a) Langer, P; Döring, M; Görls, H.; Beckert, R., Liebigs Ann./Recueil 1997, 2553.
11. (b) Langer, P.; Döring, M. Synlett 1998, 396.
12. (c) Langer, P.; Döring, M. Synlett 1998, 399.
13. (d) Langer, P; Wuckelt, J.; Döring, M; Beckert, R. Eur. J. Org. Chem. 1998, 1467.
14. (e) Seyferth, D.; Wang, T.; Langer, P.; Ostrander, R. L.; Rheingold, A. L. Organometallics 1997, 16, 2413.
15. (f) Langer, P.; Döring, M. Chem. Comm. 1998, in print.
16. Trimitsis, G. B.; Hinkley, J. M.; TenBrink, R.; Faburada, A. L.; Anderson, M.; Poli, M.; Christian, B.; Gustafson, G.; Erdman, J.; Rop, D. J. Org. Chem. 1983, 48, 2957.
17. For spiro-acetals, see: (a) Ley, S. V.; Priepke, H. W. M. Angew. Chem. 1994, 33, 2292; Ley, S. V.; Priepke, H. W. M.; Warriner, S. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 2290.
18. For spiro-acetals, see: (a) Ley, S. V.; Priepke, H. W. M. Angew. Chem. 1994, 33, 2292; Ley, S. V.; Priepke, H. W. M.; Warriner, S. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 2290.
19. (b) Ley, S. V.; Downham, R.; Edwards, P. J.; Innes, J. E.; Woods, M. Contemporary Organic Synthesis 1995, 2, 365 and literature cited herein,
20. (c) Kirby, A. J.; in: The Anomeric Effect and Related Stereochemical Effects at Oxygen, Springer: Berlin, 1983.
21. 4: C, 82.74; H, 5.01. Found: C, 82.42; H, 5.13.
22. Hay, J. V.; Portlock, D. E.; Wolfe, J. F. J. Org. Chem. 1973, 38, 4379.
23. 3-mediated reaction of 1,2-diols with oxalyl chloride decarbonylation has been reported to be stereocontrolled: Iida, T.; Itaya, T. Tetrahedron 1993, 49, 10511.
24. Langer, P.; Döring, M.; Görls, H.; Seyferth, D., unpublished results.
25. For the rearrangement of a cyclic phthalate to an orthoester in the presence of base, see: (a) Zupancic, J. J.; Horn, K. A.; Schuster, G. B. J. Am. Chem. Soc. 1980,102, 5279.
26. (b) Greene, F. D. J. Am. Chem. Soc. 1956, 78, 2250.
27. Pindur, U; Rogge, M. Heterocycles 1995, 41, 2785.
28. Carr, M. A.; Creviston, P. E.; Hutchison, D. R.; Kennedy, J. H.; Khau, V. V.; Kress, T. J.; Leanna, M. R.; Marshall, J. D.; Martinelli, M. J.; Peterson, B. C.; Varie, D. L.; Wepsiec, J. P. J Org. Chem. 1997, 62, 8640.
29. Ohno, M.; Shimizu, S.; Eguchi, S. Tetrahedron Lett. 1990, 4613.
30. (a) Malatesta, V.; Millini, R.; Montanari, L. J. Am. Chem. Soc. 1995, 117, 6258.
31. (b) Delbaere, S.; Bochu, C.; Azaroual, N.; Buntinx, G.; Vermeersch, G. J. Chem. Soc., Perkin Trans. 2 1997, 1499.
32. (c) Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197.
33. (d) Dorweiler, C.; Holderbaum, M.; Münzmay, T.; Spang, P.; Dürr, H.; Krüger, C.; Raabe, E. Chem. Ber. 1988, 121, 843.
34. Bartra, M.; Urpi, F.; Vilarrasa, J. Methods Related to the Synthesis of Macrolide Antibiotics; in: Lukacs, G.; Ohno, M. (Eds.), Recent Progress in the Chemical Synthesis of Antibiotics, Springer: Berlin, 1993.