Organocatalytic enantioselective nucleophilic vinylic substitution

Angewandte Chemie - International Edition

Volumn 45, Issue 39, 2006, Pages 6551-6554

  Poulsen, Thomas B ^a   Bernardi, Luca ^a   Bell, Mark ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Addition elimination; Asymmetric synthesis; Organocatalysis; Phase transfer catalysis; Vinylation

Indexed keywords

ADDITION-ELIMINATION; ASYMMETRIC SYNTHESIS; ORGANOCATALYSIS; PHASE-TRANSFER CATALYSIS; VINYLATION;

CATALYST SELECTIVITY; OLEFINS; PHASE TRANSITIONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CATALYSIS;

EID: 33749827801     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602275     Document Type: Article

References (40)

1. Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
2. a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840;
3. Angew. Chem. Int. Ed. 2001, 40, 3726;
4. b) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
5. Angew. Chem. Int. Ed. 2004, 43, 5138.
6. See, for example: J. Tsuji, in Palladium Reagents and Catalysts - New Perspectives for the 21st Century, 2nd ed., Wiley, New York, 2004.
7. See, for example: a) T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261;
8. b) D. J. Spielvogel, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 3500;
9. c) S. Lee, J. F. Hartwig, J. Org. Chem. 2001, 66, 3402;
10. through nucleophilic aromatic substitution, see: d) M. Bella, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 3670;
11. e) S. Kobbelgaard, M. Bella, K. A. Jørgensen, J. Org. Chem. 2006, 71, 4980.
12. a) A. Chieffi, K. Kamikawa, J. Åhman, J. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897;
13. b) T. Hamada, S. L. Buchwald, Org. Lett. 2002, 4, 999;
14. see also c) B. K. Corkey, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 17 168.
15. a) N. K. Kochetkov, L. J. Kudryashov, B. P. Gottich, Tetrahedron 1961, 63;
16. for an example of allylation through an addition - elimination mechanism, see: b) P. V. Ramachandran, S. Madhi, L. Bland-Berry, M. V. R. Reddy, M. J. O'Donnell, J. Am. Chem. Soc. 2005, 127, 13 450.
17. For a review, see, for example: a) M. J. O'Donnell in Catalytic Asymmetric Synthesis, 2nd ed (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, p. 727;
18. for recent examples of phase-transfer-catalyzed asymmetric reactions, see, for example: b) T. Ooi, Y. Uematsu, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 2548;
19. c) F. Fini, V. Sgarzani, D. Pettersen, R. P. Herrera, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 8189;
20. Angew. Chem. Int. Ed. 2005, 44, 7975;
21. d) A. Okada, T. Shibuguchi, T. Ohshima, H. Masu, K. Yamaguchi, M. Shibasaki, Angew. Chem. 2005, 117, 4640;
22. Angew. Chem. Int. Ed. 2005, 44, 4564;
23. e) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 5139;
24. f) T. Ooi, T. Miki, M. Taniguchi, M. Shiraishi, M. Takeuchi, K. Maruoka, Angew. Chem. 2003, 115, 3926;
25. Angew. Chem. Int. Ed. 2003, 42, 3981;
26. g) H.-g. Park, B.-S. Jeong, M.-S. Yoo, J.-H. Lee, M.-k. Park, Y.-J. Lee, M.-J. Kim, S.-s. Jew, Angew. Chem. 2002, 114, 3162;
27. Angew. Chem. Int. Ed. 2002, 41, 3036;
28. h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956;
29. Angew. Chem. Int. Ed. 2002, 41, 2832.
30. S. Ma, X. Lu, Z. Li, J. Org. Chem. 1992, 57, 709.
31. a) G. Modena, Acc. Chem. Res, 1971, 4, 73;
32. b) S. I. Miller, Tetrahedron 1977, 33, 1211;
33. c) Y. Apeloig, Z. Rappoport, J. Am. Chem. Soc. 1979, 101, 5095.
34. a) B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1997, 38, 8595;
35. b) E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12 414.
36. M. Miesch, G. Mislin, M. Franck-Neumann, Tetrahedron Lett. 1998, 39, 6873.
37. M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 5672.
38. Note that the change of Z to E selectivity is due to the iodine having a higher priority than the ester group according to the CIP system.
39. A. B. Lemay, K. S. Vulic, W. W. Ogilvie, J. Org. Chem. 2006, 71, 3615.
40. As noted by a referee, formation of alkynone intermediates in situ by dehydrohalogenation of 3 might also be a possible reaction pathway. Subjecting (Z)-3b to the reaction conditions resulted in the formation of trace amounts (<5%) of the alkynone, only after prolonged reaction times (>70 h). Furthermore, the reaction was carried out (with 2a) using the corresponding alkynone under otherwise identical conditions. The result obtained (4b, Z/E = 4:1, 66/40% ee; compare with Table 2, entry 3) again suggests that alkynone intermediates are not involved.