Chiral Thioimidazoline Ligands for Palladium-Catalyzed Asymmetric Allylation

Synlett

Volumn 1997, Issue 7, 1997, Pages 783-785

  Morimoto, Toshiaki ^a   Tachibana, Keijiro ^a   Achiwa, Kazuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542745046     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5785     Document Type: Article

References (31)

1. Asymmetric Reactions Catalyzed by Chiral Metal Complexes. LXXVIII.
2. Some reviews: (a) Brunner, H. In Topics in Stereochemistry; Eliel, E.; Wilen, S. H. (Ed.); John Wiley & Sons, Inc.: New York, 1988, Vol. 18, pp. 129 ff. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Method; Scheffold, R. (Ed.); Springer-Verlag, Berlin Heidelberg, 1989, pp. 115 ff. (c) Ojima, I. (Ed.) In Catalytic Asymmetric Synthesis; VCH Publishers, Inc.: New York, 1993. (d) Seyden-Penne, J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, Inc.: New York, 1995. (e) Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
3. Some reviews: (a) Brunner, H. In Topics in Stereochemistry; Eliel, E.; Wilen, S. H. (Ed.); John Wiley & Sons, Inc.: New York, 1988, Vol. 18, pp. 129 ff. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Method; Scheffold, R. (Ed.); Springer-Verlag, Berlin Heidelberg, 1989, pp. 115 ff. (c) Ojima, I. (Ed.) In Catalytic Asymmetric Synthesis; VCH Publishers, Inc.: New York, 1993. (d) Seyden-Penne, J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, Inc.: New York, 1995. (e) Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
4. Some reviews: (a) Brunner, H. In Topics in Stereochemistry; Eliel, E.; Wilen, S. H. (Ed.); John Wiley & Sons, Inc.: New York, 1988, Vol. 18, pp. 129 ff. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Method; Scheffold, R. (Ed.); Springer-Verlag, Berlin Heidelberg, 1989, pp. 115 ff. (c) Ojima, I. (Ed.) In Catalytic Asymmetric Synthesis; VCH Publishers, Inc.: New York, 1993. (d) Seyden-Penne, J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, Inc.: New York, 1995. (e) Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
5. Some reviews: (a) Brunner, H. In Topics in Stereochemistry; Eliel, E.; Wilen, S. H. (Ed.); John Wiley & Sons, Inc.: New York, 1988, Vol. 18, pp. 129 ff. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Method; Scheffold, R. (Ed.); Springer-Verlag, Berlin Heidelberg, 1989, pp. 115 ff. (c) Ojima, I. (Ed.) In Catalytic Asymmetric Synthesis; VCH Publishers, Inc.: New York, 1993. (d) Seyden-Penne, J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, Inc.: New York, 1995. (e) Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
6. Some reviews: (a) Brunner, H. In Topics in Stereochemistry; Eliel, E.; Wilen, S. H. (Ed.); John Wiley & Sons, Inc.: New York, 1988, Vol. 18, pp. 129 ff. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Method; Scheffold, R. (Ed.); Springer-Verlag, Berlin Heidelberg, 1989, pp. 115 ff. (c) Ojima, I. (Ed.) In Catalytic Asymmetric Synthesis; VCH Publishers, Inc.: New York, 1993. (d) Seyden-Penne, J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, Inc.: New York, 1995. (e) Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
7. Several non-symmetric diphosphine ligands were developed and used in efficient asymmetric hydrogenations [Some reviews: (a) Takahashi, H.; Morimoto, T.; Achiwa, K. Yuki Gousei Kagaku Kyokai Shi, 1990, 48, 29. (b) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett, 1992, 169].
8. Several non-symmetric diphosphine ligands were developed and used in efficient asymmetric hydrogenations [Some reviews: (a) Takahashi, H.; Morimoto, T.; Achiwa, K. Yuki Gousei Kagaku Kyokai Shi, 1990, 48, 29. (b) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett, 1992, 169].
9. Some reviews: (a) Trost, B. M.; van Vraken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I. (Ed.); VCH Publishers, Inc.: New York, 1993, pp. 325 ff. (e) Consiglio, G.; Waymoutu, R. M. Chem. Rev. 1989, 89, 257.
10. Some reviews: (a) Trost, B. M.; van Vraken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I. (Ed.); VCH Publishers, Inc.: New York, 1993, pp. 325 ff. (e) Consiglio, G.; Waymoutu, R. M. Chem. Rev. 1989, 89, 257.
11. Some reviews: (a) Trost, B. M.; van Vraken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I. (Ed.); VCH Publishers, Inc.: New York, 1993, pp. 325 ff. (e) Consiglio, G.; Waymoutu, R. M. Chem. Rev. 1989, 89, 257.
12. Some reviews: (a) Trost, B. M.; van Vraken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I. (Ed.); VCH Publishers, Inc.: New York, 1993, pp. 325 ff. (e) Consiglio, G.; Waymoutu, R. M. Chem. Rev. 1989, 89, 257.
13. Some reviews: (a) Trost, B. M.; van Vraken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I. (Ed.); VCH Publishers, Inc.: New York, 1993, pp. 325 ff. (e) Consiglio, G.; Waymoutu, R. M. Chem. Rev. 1989, 89, 257.
14. (a) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; J. Chem. Soc. Perkin Trans. 1, 1994, 2065.
15. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
16. (c) Chelucci, G.; Cabras, M. A. Tetrahedron Asymmetry, 1996, 7, 965.
17. (a) Kang, J.; Yu, S. H.; Kim, J. I.; Cho, H. G. Bull. Korean Chem. Soc. 1995, 16, 439.
18. (b) Enantioselectivities of PS-ligands in Rh-catalyzed hydroformylation and hydrogen transfer reduction of ketone were very low [Gladiali, S.; Dore, A.; Fabbri, D. Tetrahedron Asymmetry 1994, 5, 1143.].
19. (a) Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467.
20. (b) van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135.
21. Hiraoka, M.; Nishikawa, A.; Morimoto, T.; Achiwa, K. In Abstracts of Papers, 43rd Symposium on Organometallic Chemistry, Japan, Osaka, 1996, pp. 290-291. In Rh-catalyzed asymmetric hydrosilylation of ketones, SN-type ligands were found to have much lower enantioselectivity than PN-type ligands (ref. 10).
22. Some reviews: (a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 393. (b) Bolm, C. Angew. Chem. Int. Ed. Engl. 1991, 30, 542. (c) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
23. Some reviews: (a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 393. (b) Bolm, C. Angew. Chem. Int. Ed. Engl. 1991, 30, 542. (c) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
24. Some reviews: (a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 393. (b) Bolm, C. Angew. Chem. Int. Ed. Engl. 1991, 30, 542. (c) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
25. (a) Newman, L. M.; Williams, J. M.; McCague, R.; Potter, G. A. Tetrahedron Asymmetry 1996, 7, 1597.
26. (b) Langer, T.; Janssen, J.: Helmchen, G. Tetrahedron Asymmetry, 1996, 7, 1599.
27. Dauwe, C.; Buddrus, J. Synthesis, 1995, 171.
28. 3) δ: 1.40 (2H, m, 5-Ha, 6-Ha), 1.56 (2H, m, 4-Ha, 7-Ha), 1.85 (2H, m, 5-He, 6-He), 2.31 (2H, m, 4-He, 7-He), 2.56 (3H, s, NCH3), 3.14 (2H, m, 3a-H, 7a-H), 7.08-7.44 (9H, m, aromatic H). GC-MS (EI) m/z: 322 (M+).
29. 4. After evaporation of the solvent, the residue was purified by preparative TLC (toluene/ AcOEt= 20/1). The enantiomeric excess and the absolute configuration of the product 12 were determined by HPLC analysis with a chiral column, Chiralcel AD (hexane/2-propanol=20/1).
30. Similar thoughts on the reaction mechanism were presented [ref. 5a. Dawson, G.; Williams, M. J. Tetrahedron Asymmetry 1995, 6, 2535. Sprinz, J.; Kiefer, M.; Helmchen, G.: Reggelin, M. Tetrahedron Lett. 1994, 35, 1523.].
31. Similar thoughts on the reaction mechanism were presented [ref. 5a. Dawson, G.; Williams, M. J. Tetrahedron Asymmetry 1995, 6, 2535. Sprinz, J.; Kiefer, M.; Helmchen, G.: Reggelin, M. Tetrahedron Lett. 1994, 35, 1523.].