High enantioselectivity in rhodium-catalyzed allylic alkylation of 1-substituted 2-propenyl acetates

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1713-1715

  Hayashi, Tamio ^a   Okada, Atsushi ^a   Suzuka, Toshimasa ^a   Kawatsura, Motoi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; CARBONIC ACID; CESIUM; MALONIC ACID DERIVATIVE; NAPHTHYL GROUP; OXAZOLINE DERIVATIVE; RHODIUM;

ALKALINITY; ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0141518172     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0343562     Document Type: Article

References (40)

1. For reviews: (a) Trost, B. M.; Chulbom, L. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; p 593. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 24. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 325. (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
2. For reviews: (a) Trost, B. M.; Chulbom, L. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; p 593. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 24. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 325. (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
3. For reviews: (a) Trost, B. M.; Chulbom, L. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; p 593. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 24. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 325. (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
4. For reviews: (a) Trost, B. M.; Chulbom, L. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; p 593. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 24. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 325. (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
5. For reviews: (a) Trost, B. M.; Chulbom, L. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; p 593. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 24. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 325. (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
6. (a) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104.
7. (b) Glorius, F.; Pfaltz, A. Org. Lett. 1999, 1, 141.
8. (c) Kaiser, N.-F. K.; Bremberg, U.; Larhed, M.; Moberg, C.; Hallberg, A. Angew. Chem., Int. Ed. 2000, 39, 3596.
9. (d) Malkov, A. V.; Spoor, P.; Vinader, V.; Kocovsky, P. Tetrahedron Lett. 2001, 42, 509.
10. (e) Trost, B. M.; Dogra, K.; Hachiya, I.; Emura, T.; Hughes, D. L.; Krska, S.; Reamer, R. A.; Palucki, M.; Yasuda, N.; Reider, P. J. Angew. Chem., Int. Ed. 2002, 41, 1929. See also: Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
11. (e) Trost, B. M.; Dogra, K.; Hachiya, I.; Emura, T.; Hughes, D. L.; Krska, S.; Reamer, R. A.; Palucki, M.; Yasuda, N.; Reider, P. J. Angew. Chem., Int. Ed. 2002, 41, 1929. See also: Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
12. (a) Janssen, J. P.; Helmchen, G. Tetrahedron Lett. 1997, 38, 8025.
13. (b) Barrels, B.; Helmchen, G. Chem. Commun. 1999, 741.
14. (c) Bartels, B.; Garcia-Yebra, C.; Rominger, F.; Helmchen, G. Eur. J. Inorg. Chem. 2002, 2569. See also: Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647.
15. (c) Bartels, B.; Garcia-Yebra, C.; Rominger, F.; Helmchen, G. Eur. J. Inorg. Chem. 2002, 2569. See also: Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647.
16. (a) Tsuji, J.; Minami, I.; Shimidzu, I. Tetrahedron Lett. 1984, 25, 5157.
17. (b) Minami, I.; Shimidzu, I4 Tsuji, J. J. Organomet. Chem. 1985, 296, 269.
18. (c) Takeuchi, R.; Kitamura, N. New J. Chem. 1998, 659.
19. (a) Evans, P. A.; Nelson, J. D. Tetrahedron Lett. 1998, 39, 1725.
20. (b) Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581.
21. (c) Evans, P. A.; Kennedy, L. J. Org. Lett. 2000, 2, 2213.
22. (d) Evans, P. A.; Kennedy, L. J. J. Am. Chem. Soc. 2001, 123, 1234.
23. (e) Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609.
24. To the best of our knowledge, there has been only one report describing the use of a chiral rhodium catalyst: Selvakumar, K.; Valentini, M.; Pregosin, P. S. Organometallics 1999, 18, 4591.
25. (a) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
26. (b) Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
27. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
28. For reviews: (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336. (b) Helmchen, G. J. Organomet. Chem. 1999, 576, 203. (c) Williams, J. M. J. Synlett 1996, 705.
29. For reviews: (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336. (b) Helmchen, G. J. Organomet. Chem. 1999, 576, 203. (c) Williams, J. M. J. Synlett 1996, 705.
30. For reviews: (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336. (b) Helmchen, G. J. Organomet. Chem. 1999, 576, 203. (c) Williams, J. M. J. Synlett 1996, 705.
31. 8): δ 0.59 (d, J = 6.8 Hz, 3H), 0.96 (d, J = 7.1 Hz, 3H), 1.83 (s, 3H), 2.25 (s, 3H), 3.38 (dsep, J = 3.0, 6.9 Hz, 1H), 3.86 (dd, J = 10.0, 8.6 Hz, 1H), 4.08 (dd, J = 8.6, 4.4 Hz, 1H), 5.58 (ddd, J = 10.0, 4.4, 3.0 Hz, 1H), 5.63 (s, 1H), 7.18 (t, J = 7.5 Hz, 1H), 7.25 (d, J = 7.5 Hz, 1H), 7.27-7.30 (m, 3H), 7.34-7.41 (m, 3H), 7.50 (t, J = 8. 0 Hz, 1H), 8.01-8.07 (m, 2H), 8.10-8.17 (m, 3H).
32. 31P NMR (THF): δ 46. 6 (d, J = 143.6 Hz) for the major isomer and δ 40.7 (d, J = 148.6 Hz) for the minor isomer.
33. For a recent example of the study on the structure of the corresponding palladium complexes coordinated with the phosphino-oxazoline ligand and monosubstituted π-allyl ligands, see: Kollmar, M.; Steinhagen, H.; Janssen, J, P.; Goldefuss, B.; Makubivsjata, S. A.; Vázquez, J.; Rominger, F.; Helmchen, G. Chem. Eur. J. 2002, 8, 3103.
34. (a) Concept of extending the lifetime of a metal ally1 intermediate using slow addition has been described (ref 1).
35. (b) Effects of halide ions on the stereospecificity in rhodium-catalyzed allylic etherification have been reported: Evans, P. A.; Leahy, D. K. J. Am. Chem. Soc. 2002, 124, 7882.
36. Cesium carbonate has been used for the palladium-catalyzed asymmetric allylation forming a quaternary chiral center in nucleophiles: Trost, B. M.; Schroeder, G. M.; Kristensen, J. Angew. Chem., Int. Ed. 2002, 41, 3492.
37. (a) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron Asymmetry 1998, 9, 1779.
38. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343.
39. (c) Selvakumar, K.; Valentini, M.; Wörle, M.; Pregosin, P. S.; Albinati, A. Organometallics 1999, 18, 1207.
40. (d) Ogasawara, M.; Yoshida, K.; Hayashi, T. Heterocycles 2000, 52, 195.