Regioselective propargylation of carbonyl compounds with (3-bromo-prop-1-ynyl)trimethylsilane promoted by reactive barium

Synlett

Volumn , Issue 11, 2005, Pages 1679-1682

  Yanagisawa, Akira ^a   Okitsu, Shogo ^a   Arai, Takayoshi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Aldehydes; Barium; Ketones; Propargylation; Regioselectivity

Indexed keywords

(3 BROMOPROP 1 YLNYL)TRIMETHYLSILANE; ALKANONE; BARIUM; CYCLOPENT 2 ENONE; KETONE DERIVATIVE; METAL COMPLEX; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 22244434184     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869874     Document Type: Article

References (39)

1. Reviews: (a) Epsztein, R. In Comprehensive Carbanion Chemistry; Buncel, E.; Durst, T., Eds.; Elsevier: New York, 1984, Chap. 3, 107.
2. (b) Yamamoto, H. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford, 1991, 81.
3. (c) Marshall, J. A. Chem. Rev. 1996, 96, 31.
4. (d) Marshall, J. A. Chem. Rev. 2000, 100, 3163.
5. (e) Ferreira, F.; Denichoux, A.; Chemla, F.; Bejjani, J. Synlett 2004, 2051.
6. (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198.
7. (b) Yanagisawa, A.; Habaue, S.; Yamamoto, H. Tetrahedron 1992, 48, 1969.
8. For recent examples of regioselective propargylation of carbonyl compounds, see: (a) Mae, M.; Hong, J. A.; Hammond, G. B.; Uneyama, K. Tetrahedron Lett. 2005, 46, 1787.
9. (b) Banerjee, M.; Roy, S. Org. Lett. 2004, 6, 2137.
10. (c) Bernaud, F.; Vrancken, E.; Mangeney, P. Synlett 2004, 1080.
11. (d) Oestreich, M.; Sempere-Culler, F. Chem. Commun. 2004, 692.
12. (e) Lee, A. S.-Y.; Chu, S.-F.; Chang, Y.-T.; Wang, S.-H. Tetrahedron Lett. 2004, 45, 1551.
13. (f) Masuyama, Y.; Watabe, A.; Kurusu, Y. Synlett 2003, 1713.
14. (g) Bernaud, F.; Vrancken, E.; Mangeney, P. Org. Lett. 2003, 5, 2567.
15. (h) Shimizu, M.; Kurahashi, T.; Kitagawa, H.; Hiyama, T. Org. Lett. 2003, 5, 225.
16. (i) Banerjee, M.; Roy, S. Chem. Commun. 2003, 534.
17. For recent examples of asymmetric propargylation of carbonyl compounds, see: (j) Lai, C.; Soderquist, J. A. Org. Lett. 2005, 7, 799.
18. (k) Lee, K.-C.; Lin, M.-J.; Loh, T.-P. Chem. Commun. 2004, 2456.
19. (l) Inoue, M.; Nakada, M. Org. Lett. 2004, 6, 2977.
20. (m) Ranslow, P. B. D.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105.
21. (n) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507.
22. (o) Marshall, J. A.; Bourbeau, M. P. Org. Lett. 2002, 4, 3931.
23. (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 8955.
24. (b) Yanagisawa, A.; Habaue, S.; Yasue, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6130.
25. Reviews: (c) Yanagisawa, A.; Yamamoto, H. In Active Metals. Preparation, Characterization, Applications; Fürstner, A., Ed.; VCH: Weinheim, 1996, 61.
26. (d) Yanagisawa, A. In Science of Synthesis, Vol. 7; Yamamoto, H., Ed.; Thieme: Stuttgart, 2004, 695.
27. (e) Yanagisawa, A. In Main Group Metals in Organic Synthesis, Vol. 1; Yamamoto, H.; Oshima, K., Eds.; Wiley-VCH: Weinheim, 2004, 175.
28. (a) Sell, M. S.; Rieke, R. D. Synth. Commun. 1995, 25, 4107.
29. Reviews: (b) Rieke, R. D.; Sell, M. S.; Klein, W. R.; Chen, T.-A.; Brown, J. D.; Hanson, M. V. In Active Metals. Preparation, Characterization, Applications; Fürstner, A., Ed.; VCH: Weinheim, 1996, 1.
30. (c) Rieke, R. D.; Hanson, M. V. Tetrahedron 1997, 53, 1925.
31. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 5893.
32. Groth and coworkers reported the γ-selective addition of(trimethylsilyl)propargylmagnesium bromide to aldehydes, see: Eckenberg, P.; Groth, U.; Köhler, T. Liebigs Ann. Chem. 1994, 673.
33. (Trimethylsilyl)propargylmagnesium bromide has been reported to provide a mixture of homopropargylic alcohols and allenylic alcohols in the reaction with ketones, see: Mesnard, D.; Miginiac, L. J. Organomet. Chem. 1990, 397, 127.
34. Loh et al. have reported that regioselectivity of indium-mediated propargylation of aldehydes with trimethylsilylpropargyl bromide is improved by addition of a catalytic amount of indium tribromide or indium trifluoride. A suggested reaction mechanism involves a transition state structure similar to C, which is stabilized by coordination with a halogen of the indium species, see: Lin, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042.
35. (a) Lee, H.-Y.; Kim, B. G. Org. Lett. 2000, 2, 1951.
36. (b) Lee, H.-Y.; Kim, D.-I.; Kim, S. Bull Korean Chem. Soc. 1999, 20, 269.
37. (c) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197.
38. (a) Zhou, Z.-L.; Huang, Y.-Z.; Shi, L.-L.; Hu, J. J. Org. Chem. 1992, 57, 6598.
39. (b) Zhang, L.-J.; Mo, X.-S.; Huang, Y.-Z. J. Organomet. Chem. 1994, 471, 77.