Kinetic study of various phosphoramidite ligands in the iridium-catalyzed allylic substitution

Organic Letters

Volumn 7, Issue 8, 2005, Pages 1621-1624

  Polet, Damien ^a   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; IRIDIUM; LIGAND; PHOSPHORAMIDIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; KINETICS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 17844408116     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050350w     Document Type: Article

References (27)

1. (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; p 593.
2. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 833.
3. (c) Guiry, P. J.; Saunders: C. P. Adv. Synth. Catal. 2004, 346, 497-537.
4. (a) Prétôt, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323-325.
5. (b) Glorius, F.; Neuburger, M.; Pfaltz, A. Helv. Chim. Acta 2001, 84, 3178-3196.
6. (c) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471-7472.
7. (d) Hou, X.-L.; Sun, N. Org. Lett. 2004, 6, 4399-4401 and references cited herein.
8. For a review on Ir, see: Takeuchi, R. Synlett 2002, 1954-1965.
9. (a) Takeuchi, R.; Kashio, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 263-265.
10. (b) Battels, B.; Helmchen, G. Chem. Commun. 1999, 741-742.
11. (c) Bartels, B.; Helmchen, G.; Garcia-Yebra, C. Eur. J. Org. Chem. 2003, 1097-1103.
12. (d) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165.
13. (e) Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427.
14. (f) Shu, C.; Hartwig John, F. Angew. Chem., Int. Ed. 2004, 43, 4794-4797.
15. (g) Shu, C.; Leitner, A.; Hartwig John, F. Angew. Chem., Int. Ed. 2004, 43, 4797-4800.
16. (h) Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 116-117.
17. (i) Welter, C.; Koch, O.; Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 896-897.
18. (j) Garcia-Yebra, C.; Janssen, J. P.; Rominger, F.; Helmchen, G. Organometallics 2004, 23, 5459-5470.
19. Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272-14273.
20. Tissot-Croset, K.; Polet. D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426-2428.
21. Alexakis, A.; Polet, D. Org. Lett. 2004, 20, 3529-3532.
22. Lipowsky, G.; Miller, N.; Helmchen, G. Angew. Chem., Int. Ed. 2004, 43, 4595-4597.
23. This argument was used to justify a reaction acceleration effect in polar solvents. See ref 3 for details.
24. Work in progress.
25. Alexakis, A.; Gille, S.; Prian, F.; Rosset, S.; Ditrich, K. Tetrahedron Lett. 2004, 45, 1449-1451.
26. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
27. Lloyd-Jones, G. C.; Stephen, S. C.; Murray, M.; Butts, C. P.; Vyskocil, S.; Kocovsky, P. Chem. Eur. J. 2000, 6, 4348-4357.