Role of the planar chirality of imine-phosphine hybrid ligands bearing chromium tricarbonyl in the palladium-catalyzed asymmetric allylic alkylation

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5083-5087

  Jang, Hye Young ^a   Seo, Hwimin ^a   Han, Jin Wook ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

Allylic alkylation; Chromium tricarbonyl; Planar chirality

Indexed keywords

CHROMIUM DERIVATIVE; CHROMIUM TRICARBONYL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

EID: 0034709610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00778-4     Document Type: Article

References (27)

1. (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
2. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; p. 325.
3. (c) Heumann, A. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; pp. 251-259.
4. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
5. (e) Pretot, R.; Lloyd, G. C.; Pfaltz, A. Pure Appl. Chem. 1998, 70, 1035.
6. (f) Helmchen, G. J. Organomet. Chem. 1999, 576, 203.
7. (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
8. (b) Janssen, J. P.; Helmchen, G. Tetrahedron Lett. 1997, 38, 8025.
9. (c) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597.
10. (d) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424.
11. (a) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327.
12. (b) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091.
13. (c) Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R.; Pastó, M. Tetrahedron Lett. 1999, 40, 4977.
14. (a) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238.
15. (b) Heaton, S. B.; Jones, G. B. Tetrahedron Lett. 1993, 33, 1693.
16. (c) Jones, G. B.; Heaton, S. B. Tetrahedron: Asymmetry 1993, 4, 261.
17. (d) Hayashi, Y.; Sakai, H.; Kaneta, N.; Uemura, M. J. Organomet. Chem. 1995, 503, 143.
18. (e) Kamikawa, K.; Sugimoto, S.; Uemura, M. J. Org. Chem. 1998, 63, 8407.
19. (a) Son, S. U.; Jang, H.-Y.; Lee, I.-S.; Chung, Y. K. Organometallics 1998, 17, 3236.
20. (b) Son, S. U.; Jang, H.-Y.; Han, J. W.; Lee, I. S.; Chung, Y. K. Tetrahedron: Asymmetry 1999, 10, 347.
21. (c) Han, J. W.; Jang, H.-Y.; Chung, Y. K. Tetrahedron: Asymmetry 1999, 10, 2853.
22. (a) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765.
23. (b) Bolm, C.; Muniz-Ferrández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860.
24. Han, J. W.; Son, S. U.; Chung, Y. K. J. Org. Chem. 1997, 62, 8264. The enantiomer 2f was synthesized by the same method as the synthesis of 2e except methyl 2,3-di-O-methyl-4,6-O-(phenylmethylene)-α-D-galactopyranoside instead of (+)-4,6-O-benzylidene-α-D-glucopyranoside.
25. Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523.
26. See the supplementary material deposited at Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ.
27. Blöchl, P. E.; Togni, A. Organometallics 1996, 15, 4125.