Stereoselective synthesis of highly functionalized trisubstituted olefins via the aldol reaction of allenoxyborinates with carbonyl compounds

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5822-5825

  Yu, Su ^a   Li, Nan Sheng ^a   Kabalka, George W ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BORANE DERIVATIVE; BORON DERIVATIVE; CARBONYL DERIVATIVE; KETONE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033529821     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990080t     Document Type: Article

References (52)

1. (a) Gragg, G. M. L. Organoboranes in Organic Synthesis; Marcel Dekker: New York, 1973; pp 137-197.
2. (b) Pelter, A.; Smith K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988; pp 165-205.
3. (c) Evans, D. A.; Fu, G. C. J. Am. Chem. Soc. 1992, 114, 6671.
4. (d) Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671.
5. (e) Fisher, G. B.; Goralski, C. T.; Nicholson, L. W.; Hasha, D. L.; Zakett, D.; Singaram, B. J. Org. Chem. 1995, 60, 2026.
6. (f) Fugami, K.; Hagiware, N.; Okeda, T.; Kosugi, M. Chem. Lett. 1998, 81.
7. (g) Rochepeau-Jobron, L.; Jacquinet, J.-C. Carbohydr. Res. 1987, 303, 395.
8. (h) Panek, J. S.; Xu, F.; Rondon, A. C. J. Am. Chem. Soc. 1998, 120, 4113.
9. (a) Kabalka, G. W.; Yu, S.; Li, N.-S. Tetrahedron Lett. 1997, 38, 5455.
10. (b) Kabalka, G. W.; Yu, S.; Li, N.-S. Tetrahedron Lett. 1997, 38, 7681.
11. (c) Kabalka, G. W.; Yu, S.; Li, N.-S. Can. J. Chem. 1998, 76, 800.
12. (a) Boldrini, G. P.; Marcini, F.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1990, 1680.
13. (b) Boldrini, G. P.; Bortolotti, M.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. Tetrahedron Lett. 1991, 32, 1229.
14. Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1977, 42, 1197.
15. (a) Midland, M. M.; McDowell, D. C.; Hatch, R. L.; Tramontano, A. J. Am. Chem. Soc. 1980, 102, 867.
16. (b) Midland, M. M.; McLoughlin, J. I.; Gabriel, J. J. Org. Chem. 1989, 54, 159.
17. Ramachandran, P. V.; Teodorovic, A. V.; Rangaishenvi, M. V.; Brown, H. C. J. Org. Chem. 1992, 57, 2379.
18. Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Vilarrasa, J. J. Org. Chem. 1996, 61, 9021.
19. Kabalka, G. W.; Yu, S.; Li, N.-S.; Lipprandt, U. Tetrahedron. Lett. 1999, 40, 37.
20. (a) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1979, 44, 3888.
21. (b) Fenical, W. Chem. Rev. 1893, 93, 1673.
22. (c) Garson, M. J. Chem. Rev. 1993, 93, 1699.
23. (d) D'Auria, M. V.; Minale, L.; Riccio, R. Chem. Rev. 1993, 93, 1839.
24. (e) Uchida, K.; Utimoto, K.; Nozaki, H. Tetrahedron 1977, 33, 2987.
25. (f) Ferezou, J. P.; Berreur, J.; Meusy, J. J.; Barbier, M.; Suchy, M.; Wipf, J. K. Experentia 1977, 15, 290.
26. (g) Muller, J. M.; Fehere, H.; Gruner, J.; Boser, W. Helv. Chim. Acta 1976, 59, 2506.
27. (h) Besl, H.; Hofle, G.; Jendrny, B.; Jagers, E.; Steglich, W. Chem. Ber. 1977, 110, 3770.
28. (a) Nakata, T.; Schmide, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933.
29. (b) Corey, E. J.; Katazenellenbogen, J. A.; Gilman, N. W.; Roman, S. A.; Erickson, B. W. J. Am. Chem. Soc. 1968, 90, 5618.
30. (c) Bauchat, P.; Le Rouille, E.; Foucaud, A. Bull. Chim. Soc. Fr. 1991, 267.
31. (d) Buchholz, R.; Hoffman, H. M. R. Helv. Chim. Acta 1991, 74, 1213.
32. (e) Charette, A. B.; Cote, B. Tetrahedron Lett. 1993, 34, 6833.
33. (f) Roush, W. R.; Brown, B. B. J. Org. Chem. 1993, 58, 2151.
34. (g) Perlmutter, P.; Tabone, M. J. Org. Chem. 1995, 60, 6515.
35. (h) Marson, C. M.; Harper, S.; Oare, C. A.; Walsgrove, T. J. Org. Chem. 1998, 63, 3798.
36. (a) For a review, see: Faulkner, D. J. Synthesis 1971, 175.
37. For recent examples, see: (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, Chapter 5, Section 1, and references therein.
38. (c) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018.
39. (d) Negishi, E.; Ay M.; Gulevich, Y. V.; Noda, Y. Tetrahedron Lett. 1993, 34, 1437.
40. (e) Gao, Y.; Harada, K.; Hata, T.; Urabe, H.; Sato, F. J. Org. Chem. 1995, 60, 290.
41. (f) Deloux, L.; Srebnik, M.; Sabat, M. J. Org. Chem. 1995, 60, 3276.
42. (g) Zhang, Q.; Yang, Y.; Martin, A. R. Tetrahedron Lett. 1993, 34, 2235.
43. (h) Yang, G.; Myles, D. C. Tetrahedron Lett. 1994, 35, 2503.
44. (i) Evans, D. A.; Carreira, E. M. Tetrahedron Lett. 1990, 31, 4703.
45. (j) Ciganek, E. J. Org. Chem. 1995, 60, 4635.
46. (k) Deng, M.; Tang, Y.; Xu, W. Tetrahedron Lett. 1984, 25, 1797.
47. (l) Hanessian, S.; Beaudoin, S. Tetrahedron Lett. 1992, 33, 7655.
48. House, H. O. J. Am. Chem. Soc. 1972, 94, 8471.
49. Ma, D. W.; Yu, Y.; Lu, X. J. Org. Chem. 1989, 54, 1105.
50. Guerin, B.; Johnston, L. J. J. Org. Chem. 1989, 54, 3176.
51. Verkruijsse, H. D.; Heus-Hoos, Y. A.; Brandsma, L. J. Organometallic Chem. 1988, 338, 289
52. Barbee, T. R.; Albizati, K. F. J. Org. Chem. 1991, 56, 6764.