Synthesis of an ethynyl carbamate and application for enantioselective cyclocarbolithiation

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2193-2195

  Gralla, Gabriele ^a   Wibbeling, Birgit ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0042529331     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0260674     Document Type: Article

References (40)

1. (a) Hoppe, D.; Hintze, F.; Tebben, P. Angew. Chem. 1990, 102, 1457-1459;
2. Angew. Chem., Int. Ed. Engl. 1990, 29, 1422-1423.
3. (b) Review: Hoppe, D.; Hense, T. Angew. Chem. 1997, 109, 2376-2410;
4. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316.
5. Beak, P.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
6. Reviews: (a) Marek, I.; Normant, J. F. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 271-337.
7. (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911.
8. (c) Review: Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544.
9. (d) Bailey, W. F.; Carson, M. W. J. Org. Chem. 1998, 2, 361-365.
10. (e) Bailey, W. F.; Mealy, M. J. J. Am. Chem. Soc. 2000, 122, 6787-6788.
11. For the 5-exo-trig ring closure, see: (a) Woltering, M. J.; Fröhlich, R.; Hoppe, D. Angew. Chem. 1997, 109, 1804-1805; Angew. Chem., Int. Ed. Engl. 1997, 29, 1764-1766.
12. For the 5-exo-trig ring closure, see: (a) Woltering, M. J.; Fröhlich, R.; Hoppe, D. Angew. Chem. 1997, 109, 1804-1805; Angew. Chem., Int. Ed. Engl. 1997, 29, 1764-1766.
13. (b) Woltering, M. J.; Fröhlich, R.; Wibbeling, B.; Hoppe, D. Synlett 1998, 797.
14. (c) Hoppe, D., Woltering, M. J.; Oestreich, M.; Fröhlich, R. Helv. Chim. Acta 1999, 82, 1860.
15. For the 5-exo-dig ring closure, see: (a) Oestreich, M.; Fröhlich, R.; Hoppe, D. Tetrahedron Lett. 1998, 39, 1745-1748.
16. (b) Oestreich, M.; Fröhlich, R.; Hoppe, D. Tetrahedron Lett. 1999, 40, 1881-1884.
17. (c) Oestreich, M.; Fröhlich, R.; Hoppe, D. J. Org. Chem. 1999, 64, 8616-8626.
18. Funk, R. L.; Bolton, G. L.; Brummond, K. M.; Ellestad, K. E.; Stallman, J. B. J. Am. Chem. Soc. 1993, 115, 7023-7024.
19. (a) Kocienski, P.; Dixon, N. J. Synlett 1989, 52.
20. (b) Sengupta, S.; Snieckus, V. J. Org. Chem. 1990, 55, 5680-5683.
21. Peschke, B. Dissertation, Universität Kiel, 1991.
22. (a) For the preparation of ynol ethers, see: Brandsma, L.; Bos, H. J. T.; Arens, J. F. Chemistry of Acetylenes; Marcel Dekker: New York, 1969; p 751.
23. (b) Nakai, T.; Tanaka, K.; Shiraishi, S.; Ishikawa, N. Tetrahedron Lett. 1978, 34, 3103-3106.
24. (c) Moyano, A.; Carbonnier, F.; Greene, A. E. J. Org. Chem. 1987, 52, 2919.
25. (d) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: New York, 1988; pp 171, 174.
26. (e) Danheiser, R. L.; Nishida, A.; Savariar, S.; Trova, M. Tetrahedron Lett. 1988, 29, 4917-4920.
27. (a) Hoppe, D.; Riemenschneider, C.; Angew. Chem. 1983, 95, 64-65; Angew. Chem., Int. Ed. Engl. 1983, 22, 54-55.
28. (a) Hoppe, D.; Riemenschneider, C.; Angew. Chem. 1983, 95, 64-65; Angew. Chem., Int. Ed. Engl. 1983, 22, 54-55.
29. (b) Hoppe, D.; Gonschorrek, C.; Schmidt, D.; Egert, E. Tetrahedron 1987, 43, 2457-2466.
30. The reaction of 4 with 3.5 equiv of LDA afforded 7 in 56% yield.
31. For the preparation of 2,2-difluorovinyl carbamates, see: (a) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289-10302.
32. (b) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron Lett. 1996, 37, 5975-5978.
33. (c) Balnaves, A. S.; Palmer, M. J.; Percy, J. M.; Rock, M. H. Chem. Commun. 1999, 2183-2184.
34. Christoph, G.; Hoppe, D. Org. Lett. 2002, 4, 2189-2192.
35. Further examples: (a) Tomooka, K.; Komine, N.; Nakai, T. Tetrahedron Lett. 1997, 38, 8939-8942.
36. (b) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322-5323.
37. (c) Coldham, I.; Fernandez, J. C.; Price, K. N. J. Org. Chem. 2000, 65, 3788-3795.
38. (d) Coldham, I.; Hufton, R.; Price, K. N.; Rathmell, R. E.; Snowden, D. J.; Vennall, G. P. Synthesis 2001, 1523-1531.
39. (e) Serino, C.; Stehle, N.; Park, Y. S.; Florio, S.; Beak, P. J. Org. Chem. 1999, 64, 1160-1165.
40. Crystals suitable for X-ray diffraction analysis were grown by vapor diffusion of pentane into an ethereal solution of cis-17.