Straightforward synthesis of allylated keto esters: The palladium-catalysed haloketone alkoxycarbonylation/allylation domino reaction

Advanced Synthesis and Catalysis

Volumn 354, Issue 6, 2012, Pages 1077-1083

  Wahl, Benoit ^a   Giboulot, Steven ^b   Mortreux, André ^a   Castanet, Yves ^a   Sauthier, Mathieu ^a   Liron, Frédéric ^b   Poli, Giovanni ^b  

^a UNIV LILLE   (France)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

allylic alkylation; carbon monoxide; catalysis; domino reaction; selectivity

Indexed keywords

EID: 84859946682     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100848     Document Type: Article

References (39)

1. R. A. Sheldon, Chemtech 1994, 24, 38-47
2. K. H. Shaughnessy, R. B. DeVasher, Curr. Org. Chem. 2005, 9, 585-604.
3. L. F. Tietze, Chem. Rev. 1996, 96, 115-136
4. L. F. Tietze, G. Brasche, K Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006.
5. Otherwise named cascade or tandem reactions.
6. G. P. Chiusoli, M. Costa, in: Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.:, E. Negishi,), John Wiley & Sons, Hoboken, N.J., 2002, Vol. 2, pp2595- 2621
7. X.-F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev., 2011, 40, 4986, and references quoted therein.
8. A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289.
9. Topics in Organometallic Chemistry, (Ed.:, M. Beller,), Vol 18, Springer-Verlag, Berlin, Heidelberg, 2006.
10. I. M. Brinza, A. G. Fallis, J. Org. Chem. 1996, 61, 3580-3581
11. S. Tsunoi, I. Ryu, S. Yamasaki, M. Tanaka, N. Sonoda, M. Komatsu, Chem. Commun. 1997, 1889-1890
12. I. Ryu, H. Kuriyama, S. Minakata, M. Komatsu, J.-Y. Yoon, S. Kim, J. Am. Chem. Soc. 1999, 121, 12190-12191
13. K. Miura, M. Tojino, N. Fujisawa, A. Hosomi, I. Ryu, Angew. Chem. 2004, 116, 2477-2479
14. Angew. Chem. Int. Ed. 2004, 43, 2423-2425.
15. M. D. Mihovilovic, P. Stanetty, Angew. Chem. 2007, 119, 3684-3688
16. Angew. Chem. Int. Ed. 2007, 46, 3612-3615.
17. A. R. Siamaki, B. A. Arndtsen, J. Am. Chem. Soc. 2006, 128, 6050-6051.
18. R. Dhawan, R. D. Dghaym, D. J. St. Cyr, B. A. Arndtsen, Org. Lett. 2006, 8, 3927-3930.
19. T. Sugihara, C. Copéret, Z. Owczarczyk, L. S. Harring, E.-I. Negishi, J. Am. Chem. Soc. 1994, 116, 7923- 7924
20. E.-i. Negishi, G. Wang, G. Zhu, Top. Organomet. Chem, 2006, 19, 1-48.
21. N. Jeong, S. D. Seo, J. Y. Shin, J. Am. Chem. Soc. 2000, 122, 10220-10221
22. S. U. Son, K. H. Park, Y. K. Chung, J. Am. Chem. Soc. 2002, 124, 6838-6839.
23. G. Poli, G. Giambastiani, Tetrahedron 2000, 56, 5959-5989
24. G. Poli, G. Giambastiani, J. Org. Chem. 2002, 67, 9456-9459
25. G. Prestat, G. Poli, Chemtracts: Org. Chem. 2004, 17, 97-103.
26. J. K. Stille, P. K. Wong, J. Org. Chem. 1975, 40, 532-534
27. S. R. Adapa, C. S. N. Prasad, J. Chem. Soc. Perkin Trans. 1 1989. 1, 1706- 1707.
28. J. R. Zoeller, European Patent Application, EP 1 676 830 A1, 2005
29. A. L. Lapidus, O. L. Eliseev, T. N. Bondarenko, O. E. Sizan, E. G. Ostapenko, I. P. Beletskaya, Kinet. Catal. 2004, 45, 234-238
30. G. Cavinato, L. Toniolo, J. Mol. Catal. A: Chem. 1999, 143, 325- 330.
31. β-Keto esters can undergo Pd-catalysed allylation under base-free conditions:, G. Giambastiani, G. Poli, J. Org. Chem. 1998, 63, 9608-9609.
32. T. Mandai, in: Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.:, E.-I. Negishi,), Vol 2, Chapt.V.2.2, pp1845-1858, Wiley, New York, 2002
33. Z. Liu, H. Du, Org. Lett. 2010, 12, 3054-3057
34. C. Goux, M. Massacret, P. Lhoste, D. Sinou, Organometallics 2008, 27, 585 -4593
35. H. Kim, C. Lee, Org. Lett. 2002, 4, 4, 4369- 4371.
36. S.-I. Murahashi, Y. Imada, Y. Taniguchi, S. Higashiura, J. Org. Chem. 1993, 58, 1538-1545
37. R. J. vanHaaren, H. Oevering, P. C. J. Kamer, K. Goubitz, J. Fraanje, P. W. N. M. vanLeeuwen, G. P. F. vanStrijdonck, J. Organomet. Chem. 2004, 689, 3800-3805.
38. J. Tsuji, Y. Kobayashi, H. Kataoka, T. Takahashi, Tetrahedron Lett. 1980, 21, 1475-1478
39. R. Moser, T. Nishikata, B. H. Lipshutz, Org. Lett. 2010, 12, 28-31.