Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to a-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8799-8804

  Paquette, Leo A ^a,b   Mitzel, Thomas M ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b TRINITY COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039874886     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9613489     Document Type: Article

References (47)

1. Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993,93,2207.
2. (b) Roush, W. R. In Comprehensive Organic Synthesis; Heathcock, C., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 1.
3. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987,26, 489.
4. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985,24, 1.
5. (e) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984,23,556.
6. (f) Reetz, M. T. Ace. Chem. Res. 1993, 26, 462.
7. Denmark, S. E.; Weber, E. J. Helv. Chim. Ada 1983, 66, 1655.
8. (a) Li, C.-J. Tetrahedron 1996,52, 5643.
9. (b) Li, C.-J. Chem. Rev. 1993,93,2023.
10. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
11. (a) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, Ç863.
12. (b) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996,118, 1917.
13. Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996,118, 1931.
14. Isaac, M. B.; Chan, T.-H. Tetrahedron Lett. 1995, 36, 8957.
15. Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pirrung, M. C.; White, C. T.; VanDerveer, D. J. Org. Chem. 1980, 45, 3846.
16. Martin, S. F; Li, W. J. Org. Chem. 1989, 54, 6129. The compilations of 13C NMR shifts provided for 6 and 8 in this paper are incomplete. As shown herein, the syn.syn isomer exhibits a necessary 12th carbon peak at 126.5 ppm. For the anti,anti isomer, the unlisted carbon signal is seen at 127.0 ppm.
17. Schlosser, M.; Brich, Z. Helv. Chlm. Acta 1978, 61, 1903.
18. Chen, D.-L.; Li, C.-J. Tetrahedron Lett. 1996, 37, 295.
19. (a) Li, C.-J.; Chan, T.-H. Can. J. Chem. 1992, 70, 2726.
20. (b) Hoffmann, R. W.; Metternich, R.; Lanz, J. W. LiebigsAnn Chem. 1987, 881.
21. (a) Still, W. C; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031.
22. (b) Still, W. C.; Schneider, J. A. Tetrahedron Lett. 1984,25, 729.
23. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
24. (b) Ahn, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, l, 61.
25. Selected examples include the following: (a) Williams, D. R.; Klingler, F. D. Tetrahedron Lett. 1987, 28, 869.
26. (b) Roush, W. R.; Peseckis, S. M.; Walts, A. C. J. Org. Chem. 1984, 49, 3429.
27. Roush, W. R.; Harris, D. J.; Lesur, B. M. Tetrahedron Lett. 1983,24,2227.
28. Wuts, P. G. M.; Bigelow, S. S. J. Org. Chem. 1983, 48, 3489.
29. (e) Hoffmann, R. W.; Zeiss, H.-J.; Ladner, W.; Tabche, S. Chem. Ber. 1982, 115,2357.
30. (f) Fujita, K.; Schlosser, M. Helv. Chim. Ada 1982,65,1258.
31. (g) Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1981, 703,3229.
32. (h) Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1980, 1072.
33. (a) Nordlander, J. E.; Roberts, J. D. J. Am. Chem. Soc. 1959, 81, 1769.
34. (b) Nordlander, J. E.; Young, W. G.; Roberts, J. D. J. Am. Chem. Soc. 1961, 83, 494.
35. Whitesides, G. M.; Nordlander, J. E.; Roberts, J. D. J. Am. Chem. Soc. 1984, 84, 2010.
36. (a) Schlosser, M.; Hartmann, J. Angew. Chem., Int. Ed. Engl. 1973, 12, 439.
37. (b) Hartmann, J.; Muthukrishnan, R.; Schlosser, M. Helv. Chim. Acta 1974,57, 2261.
38. Schlosser, M. Angew. Chem., Int. Ed. Engl. 1974,13, 701.
39. Schlosser, M.; Hartmann, J. J. Am. Chem. Soc. 1976, 98, 4674.
40. (a) West, P.; Purmont, J. I.; McKinley, S. V. J. Am. Chem. Soc. 1968,90,797.
41. (b) Bates, R. B.; Beavers, W. A. J. Am. Chem. Soc. 1974, 96, 5001.
42. (a) Sandel, V. R.; McKinney, S. V.; Freedman, H. H. J. Am. Chem. Soc. 1968, 90, 495.
43. (b) Schlosser, M. Chimia 1974,28, 395.
44. Schlosser, M.; Hartmann, J.; David, V. Helv. Chim. Acta 1974, 57, 2261.
45. Rauchschwalbe, G.; Schlosser, M. Helv. Chim. Acta 1975, 58, 1094.
46. For general experimental details, consult ref 4b.
47. Heathcock, C. H.; Kiyooka, S.; Blumenkopf, T. A. J. Org. Chem. 1984, 49, 4214.