Carbocycles via enantioselective inter- and intramolecular iridium-catalysed allylic alkylations

Chemical Communications

Volumn , Issue 23, 2005, Pages 2957-2959

  Streiff, Stephane ^a   Welter, Carolin ^a   Schelwies, Mathias ^a   Lipowsky, Gunter ^a   Miller, Nicole ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; IRIDIUM;

ALKYLATION; ARTICLE; CATALYSIS; ENANTIOMER; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; REACTION ANALYSIS; RING CLOSING METATHESIS;

EID: 21444438132     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b503713a     Document Type: Article

References (30)

1. (a) B. M. Trost and C. Lee, in Catalytic Asymmetric Synthesis, ed. I. Ojima, Wiley, New York, 2000, 2nd edn., p. 593;
2. (b) A. Pfaltz and M. Lautens, in Comprehensive Asymmetric Catalysis I-III, ed. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin, 1999, p. 833;
3. (c) B. M. Trost and M. L. Crawley, Chem. Rev., 2003, 103, 2921.
4. (a) B. Bartels and G. Helmchen, Chem. Commun., 1999, 741;
5. (b) B. Bartels, C. Garcia-Yebra, F. Rominger and G. Helmchen, Eur. J. Inorg. Chem., 2002, 2569;
6. (c) G. Lipowsky, N. Miller and G. Helmchen, Angew. Chem., Int. Ed., 2004, 43, 4595;
7. (d) G. Lipowsky and G. Helmchen, Chem. Commun., 2004, 116;
8. (e) A. Alexakis and D. Polet, Org. Lett., 2004, 6, 3529;
9. (f) K. Tissot-Croset, D. Polet and A. Alexakis, Angew. Chem., Int. Ed., 2004, 43, 2426.
10. (a) C. Welter, O. Koch, G. Lipowsky and G. Helmchen, Chem. Commun., 2004, 896;
11. (b) A. Leitner, C. Shu and J. F. Hartwig, Proc. Natl. Acad. Sci. USA, 2004, 101, 5930;
12. (c) C. Shu, A. Leitner and J. F. Hartwig, Angew. Chem., Int. Ed., 2004, 43, 4797.
13. (a) F. Lopez, T. Ohmura and J. F. Hartwig, J. Am. Chem. Soc., 2003, 125, 3426;
14. (b) Kinetic resolution: C. Fischer, C. Defieber, T. Suzuki and E. M. Carreira, J. Am. Chem. Soc., 2004, 126, 1628.
15. The world market prices per ounce (October 2003) are: rhodium $500, palladium $199, iridium $90.
16. Survey: B. L. Feringa, Acc. Chem. Res., 2000, 33, 346.
17. B. Bartels, C. Garcia-Yebra and G. Helmchen, Eur. J. Org. Chem., 2003, 1097.
18. Other ligands probed have been phosphites (cf. N. Kinoshita, K. H. Marx, K. Tanaka, K. Tsubaki, T. Kawabata, N. Yoshikai, E. Nakamura and K. Fuji, J. Org. Chem, 2004, 69. 7960 and literature cited therein);
19. phosphinooxazolines (ref. 3a) and Pybox (H. Miyabe, A. Matsumura, K. Moriyama and Y. Takemoto, Org. Lett., 2004, 6, 4631).
20. TBD: 1,5,7-triazabicyclo[4.4.0]dec-5-ene; DABCO: 1,4-diazabicyclo-[2.2.2] octane.
21. C. A. Kiener, C. Shu, C. Incarvito and J. F. Hartwig, J. Am. Chem. Soc., 2003, 125, 14272.
22. P. A. Evans et al. have reported a similar regioselective but not enantioselective Rh-catalysed allylic alkylation, using alkenylmalonates as nucleophiles, followed by RCM to furnish monocyclic carbocycles: (a) P. A. Evans and L. J. Kennedy, Tetrahedron Lett., 2001, 42, 7015;
23. see also B. M. Trost and C. Jiang, Org. Lett., 2003, 5, 1563.
24. An asymmetric Cu-catalysed allylic substitution/RCM sequence was reported by the Alexakis group: K. Tisot-Croset, D. Polet, S. Gille, C. Hawner and A. Alexakis, Synthesis, 2004, 2586.
25. 2Ru=CHPh, cf. P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1995, 34, 2039.
26. In this case, use of procedure D did not lead to improvement.
27. C. Welter, A. Dahnz, B. Brunner, S. Streiff, P. Dübon and G. Helmchen, Org. Lett., 2005, 7, 1239.
28. G. Helmchen and A. Pfaltz, Acc. Chem. Res., 2000, 6, 336.
29. 8: G. Koch and A. Pfaltz, Tetrahedron: Asymmetry, 1996, 7, 2213;
30. 9: M. Peer, Dissertation, Universität Heidelberg, Heidelberg, Germany, 1996.