Anomalous threo-diastereoselectivity in allylic silane- or stannane-aldehyde condensation reactions: New interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 17, 1990, Pages 1161-1163

  Mikami, Koichi ^a   Kawamoto, Kazuya ^a   Loh, Teck Peng ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049067086     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39900001161     Document Type: Article

References (20)

1. Y. Yamamoto, Acc. Chem. Res., 1987, 20, 243.
2. R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1982, 21, 555.
3. A. Hosomi, Acc. Chem. Res., 1988, 21, 200.
4. T. Hiyama, J. Synth. Org. Chem. Jpn., 1981, 39, 81.
5. H. Sakurai, Synlett., 1989 1.
6. T. Hayashi, M. Konishi and M. Kumada, J. Am. Chem. Soc., 1982, 104, 4963.
7. G. E. Keck and E. P. Boden, Tetrahedron Lett., 1984, 25, 1879.
8. S. E. Denmark and E. J. Weber, Helv. Chim. Acta., 1983, 66, 1655.
9. S. E. Denmark and E. J. Weber, J. Am. Chem. Soc., 1984, 106, 7970.
10. K. Mikami, T. Maeda, N. Kishi and T. Nakai, Tetrahedron Lett., 1984, 25, 5151. The problem is the relative preference of the antiperiplanar Avs. the other synclinal conformation B
11. K. Mori, J. Synth. Org. Chem. Jpn., 1985, 43, 849.
12. N. B. Mandava, Annu. Rev. Plant Physiol. Plant Mol. Biol., 1988, 39, 23.
13. M. T. Reetz, Angew. Chem., Int. Ed. Engl., 1984, 23, 556.
14. M. T. Reetz, K. Kesseler and A. Jung, Tetrahedron, 1984, 40, 4327.
15. K. Mikami, T.-P. Loh and T. Nakai, Tetrahedron Asymmetry, 1990, 1, 13.
16. C. H. Heathcock, in ‘Asymmetric Synthesis,’ ed. J. D. Morrison, Academic Press, Orlando, 1984, vol. 3.
17. C. S. Wilcox and R. E. Babston, J. Org. Chem., 1984, 49, 1451.
18. C. Gennari, M. Beretta, A. Bernardi, G. Moro, C. Scolastico and R. Todeschini, Tetrahedron, 1986, 42, 893.
19. F. Johnson, Chem. Rev., 1968, 68, 375.
20. R. W. Hoffmann, Chem. Rev., 1989, 89, 1841.