No.105
Chiral Ligands
| B1614 | (-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl- 1,3-dioxolane (1a) |
5g |
| B2048 | (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane (1b) |
5g 1g |
Chiral ligand 1 is used for enantioselective addition of Grignard reagents to ketones which affords tertiary alcohols with high optical yields1). Furthermore, a variety of titanium complexes may be prepared from 1, and the titanium complexes are used for asymmetric allylation reactions2), asymmetric alkylation reactions3), asymmetric iodocarbocyclization reactions4), and asymmetric Diels-Alder reactions5) etc.
References
1) Asymmetric addition of primary alkyl Grignard reagents to ketones
B. Weber, D. Seebach, Angew. Chem. Int. Ed. Engl., 31, 84 (1992).
2) Asymmetric allylation of aldehydes
A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. R.-Streit, F. Schwarzenbach, J. Am. Chem. Soc., 114, 2321 (1992).
3) Asymmetric alkylation of aldehydes
B. Schmidt, D. Seebach, Angew. Chem. Int. Ed. Engl., 30, 99 (1991).
D. Seebach, L. Behrendt, D. Felix, ibid., 30, 1008 (1991).
D. Seebach, D. A. Plattner, A. K. Beck, Y. M. Wang, D. Hunziker, W. Petter, Helv. Chim. Acta, 75, 2171 (1992).
4) Asymmetric iodocarbocyclization
T. Inoue, O. Kitagawa, O. Ochiai, M. Shiro, T. Taguchi, Tetrahedron Lett., 36, 9333 (1995).
5) Asymmetric Diels-Alder reaction
K. Narasaka, M. Inoue, N. Okada, Chem. Lett., 1986, 1109.
B. Weber, D. Seebach, Angew. Chem. Int. Ed. Engl., 31, 84 (1992).
2) Asymmetric allylation of aldehydes
A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. R.-Streit, F. Schwarzenbach, J. Am. Chem. Soc., 114, 2321 (1992).
3) Asymmetric alkylation of aldehydes
B. Schmidt, D. Seebach, Angew. Chem. Int. Ed. Engl., 30, 99 (1991).
D. Seebach, L. Behrendt, D. Felix, ibid., 30, 1008 (1991).
D. Seebach, D. A. Plattner, A. K. Beck, Y. M. Wang, D. Hunziker, W. Petter, Helv. Chim. Acta, 75, 2171 (1992).
4) Asymmetric iodocarbocyclization
T. Inoue, O. Kitagawa, O. Ochiai, M. Shiro, T. Taguchi, Tetrahedron Lett., 36, 9333 (1995).
5) Asymmetric Diels-Alder reaction
K. Narasaka, M. Inoue, N. Okada, Chem. Lett., 1986, 1109.
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