Palladium-catalyzed enantioselective allylic alkylations through C-H activation

Angewandte Chemie - International Edition

Volumn 52, Issue 5, 2013, Pages 1523-1526

  Trost, Barry M ^a   Thaisrivongs, David A ^a   Donckele, Etienne J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

allylic alkylation; C H activation; enantioselectivity; homogeneous catalysis; palladium

Indexed keywords

ALLYLIC ALKYLATION; ALLYLIC SUBSTITUTION; C-H ACTIVATION; ENANTIOSELECTIVE; HOMOGENEOUS CATALYSIS; PALLADIUM-CATALYZED; PHOSPHORAMIDITE LIGANDS; QUATERNARY CARBON;

ALLYLATION; BIOCHEMISTRY; ENANTIOSELECTIVITY; LIGANDS; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS;

ACTIVATION ANALYSIS;

CARBON; HYDROGEN; LIGAND; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKYLATION; CARBON; CATALYSIS; HYDROGEN; LIGANDS; PALLADIUM; STEREOISOMERISM;

EID: 84872868015     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207870     Document Type: Article

References (43)

1. B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422
2. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2944
3. B. M. Trost, J. Org. Chem. 2004, 69, 5813-5837
4. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264-303
5. Angew. Chem. Int. Ed. 2008, 47, 258-297
6. B. M. Trost, T. Zhang, J. D. Sieber, Chem. Sci. 2010, 1, 427-440.
7. H. Yorimitsu, K. Oshima, Angew. Chem. 2005, 117, 4509-4513
8. Angew. Chem. Int. Ed. 2005, 44, 4435-4439
9. A. Alexakis, J. E. Bäckvall, N. Krause, O. Pàmies, M. Diéguez, Chem. Rev. 2008, 108, 2796-2823
10. C. A. Falciola, A. Alexakis, Eur. J. Org. Chem. 2008, 3765-3780.
11. G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies, R. Wiehofen, Chem. Commun. 2007, 675-691
12. J. F. Hartwig, L. M. Stanley, Acc. Chem. Res. 2010, 43, 1461-1475.
13. B. M. Trost, J. R. Miller, C. M. Hoffman, Jr., J. Am. Chem. Soc. 2011, 133, 8165-8167, and references therein.
14. B. M. Trost, C. Jäkel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438-4439
15. B. M. Trost, J. Xie, J. Am. Chem. Soc. 2006, 128, 6044-6045.
16. J. Tsuji, Acc. Chem. Res. 1969, 2, 144-152
17. B. M. Trost, Tetrahedron 1977, 33, 2615-2649.
18. For a singular example of a palladium(0)-catalyzed allylic C-H alkylation of propene and 1-butene under reducing conditions, see:, L. S. Hegedus, T. Hayashi, W. H. Darlington, J. Am. Chem. Soc. 1987, 100, 7747-7748. For a non-asymmetric copper- and cobalt-catalyzed cross-dehydrogenative-coupling reaction of allylic C-H bonds and activated methylenes, see
19. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 56-57.
20. M. S. Chen, M. C. White, J. Am. Chem. Soc. 2004, 126, 1346-1347.
21. S. Lin, C.-X. Song, G.-X. Cai, W.-H. Wang, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 12901-12903.
22. A. J. Young, M. C. White, J. Am. Chem. Soc. 2008, 130, 14090-14091.
23. A. J. Young, M. C. White, Angew. Chem. 2011, 123, 6956-6959
24. Angew. Chem. Int. Ed. 2011, 50, 6824-6827.
25. J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732
26. Angew. Chem. Int. Ed. 2001, 40, 4591-4597
27. I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105-10146
28. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2007, 5969-5994
29. M. Bella, T. Gasperi, Synthesis 2009, 1583-1614.
30. B. M. Trost, M. R. Machacek, A. Aponick, Acc. Chem. Res. 2006, 39, 747-760.
31. Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications (Ed.:, A. Börner,), Wiley-VCH, New York, 2008.
32. D. J. Covell, M. C. White, Angew. Chem. 2008, 120, 6548-6551
33. Angew. Chem. Int. Ed. 2008, 47, 6448-6451.
34. B. M. Trost, M. M. Hansmann, D. A. Thaisrivongs, Angew. Chem. 2012, 124, 5034-5037
35. Angew. Chem. Int. Ed. 2012, 51, 4950-4953
36. B. M. Trost, D. A. Thaisrivongs, Angew. Chem. 2012, 124, 11690-11694
37. Angew. Chem. Int. Ed. 2012, 51, 11522-11526.
38. B. M. Trost, J. P. Stambuli, S. M. Silverman, U. Schwörer, J. Am. Chem. Soc. 2006, 128, 13328-13329.
39. The relative stereochemistry of these transformations was assigned by analogy to reactions described by Wistrand and Skrinjar. With these sets of reaction conditions, trans-substituted pyrrolidines are always the major products. See:, L.-G. Wistrand, M. Skrinjar, Tetrahedron 1991, 47, 573-582. Similarly trans-selective cuprate additions have been observed by many groups. For examples, see
40. I. Collado, J. Ezquerra, C. Pedregal, J. Org. Chem. 1995, 60, 5011-5015
41. Y. Tong, Y. M. Fobian, M. Wu, N. D. Boyd, K. D. Moeller, J. Org. Chem. 2000, 65, 2484-2493
42. R. G. Vaswani, A. R. Chamberlin, J. Org. Chem. 2008, 73, 1661-1681. See the Supporting Information for details.
43. R. Kuwano, K. Uchida, Y. Ito, Org. Lett. 2003, 5, 2177-2179.