Stereoselective carbonyl allylation by umpolung of allylpalladium(II) complexes

European Journal of Organic Chemistry

Volumn , Issue 22, 2007, Pages 3599-3611

  Zanoni, Giuseppe ^a   Pontiroli, Alessandro ^b   Marchetti, Alberto ^a   Vidari, Giovanni ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b NONE   (Italy)

Author keywords

Allyl ligands; Allylation; Chiral monoligands; Palladium; Umpolung

Indexed keywords

EID: 34547699738     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700054     Document Type: Short Survey

References (32)

1. a) J. Tsuji, Perspectives in Organopalladium Chemistry for the 21st Century, Elsevier, Amsterdam, 1999;
2. b) J. Tsuji, Palladium Reagents and Catalysis: Innovations in Organic Synthesis, Wiley, Chichester, 1995;
3. c) E. Negishi, A. de Meijere, Organopalladium Chemistry for Organic Synthesis, vol. 2, John Wiley & Sons, New York, 2002.
4. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
5. S. E. Denmark, N. G. Almstead, Allylation of Carbonyls: Methodology and Stereochemistry in Modern Carbonyl Chemistry (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000.
6. a) Y. Masuyama, N. Kinugawa, Y. Kurusu, J. Org. Chem. 1987, 52, 3702-3704;
7. b) Y. Masuyama, K. Otake, Y. Kurusu, Tetrahedron Lett. 1988, 29, 3563-3599;
8. c) Y. Masuyama, K. Otake, Y. Kurusu, J. Chem. Soc. Chem. Commun. 1988, 44-45.
9. J. P. Takahara, Y. Masuyama, Y. Kurusu, J. Am. Chem. Soc. 1992, 114, 2577-2586.
10. Y. Masuyama, K. Otake, Y. Kurusu, Tetrahedron Lett. 1988, 29, 3563-3566.
11. Y. Masuyama, A. Ito, Y. Kurusu, Chem. Commun. 1998, 315-316.
12. a) W. Lee, K.-H. Kim, M. D. Surman, M. J. Miller, J. Org. Chem. 2003, 68, 139-149;
13. b) R. Yanada, A. Kaieda, Y. Takemoto, J. Org. Chem. 2001, 66, 7516-7518;
14. c) T. Hirashita, T. Kamei, M. Satake, T. Horie, H. Shimizu, S. Araki, Org. Biomol. Chem. 2003, 1, 3799-3803.
15. J. A. Marshall, L. M. McNulty, D. Zou, J. Org. Chem. 1999, 64, 5193-5200.
16. Araki, T. Kamei, T. Hirashita, H. Yamamura, M. Kawai, Org. Lett. 2000, 2, 847-849.
17. S. Araki, K. Kameda, J. Tanaka, T. Hirashita, H. Yamamura, M. Kawai, J. Org. Chem. 2001, 66, 7919-7921.
18. M. Anzai, R. Yanada, N. Fujii, H. Ohno, T. Ibuka, Y. Takemoto, Tetrahedron 2002, 58, 5231-5239.
19. Y. Tamaru, J. Organomet. Chem. 1999, 576, 215-231.
20. Y. Tamaru, A. Tanaka, K. Yasui, S. Goto, S. Tanaka, Angew. Chem. Int. Ed. Engl. 1995, 34, 787-789.
21. H. Nakamura, H. Iwama, Y. Yamamoto, J. Am. Chem. Soc. 1996, 118, 6641-6647.
22. O. A. Wallner, K. Szabó, Chem. Eur. J. 2003, 9, 4025-4030.
23. H. Kurosawa, A. Urabe, K. Miki, N. Kasai, Organometallics 1986, 5, 2002-2008.
24. N. Solin, J. Kjellgren, K. Szabó, J. Am. Chem. Soc. 2004, 126, 7026-7033.
25. Szabò has reported an asymmetric allylation by boronate/palladium/umpolung using a chiral auxiliary on boron: S. Sebelius, K. Szabó, Eur. J. Org. Chem. 2005, 70, 2539-2547.
26. a) G. Zanoni, S. Gladiali, A. Marchetti, P. Piccinini, I. Tredici, G. Vidari, Angew. Chem. Int. Ed. 2004, 43, 846-849;
27. b) G. P. Howell, A. J. Minnaard, B. L. Feringa, Org. Biomol. Chem. 2006, 4, 1278-1283.
28. G. C. Lloyd-Jones, S. C. Stephen, M. Murray, C. B. Butts, S. Vyskočil, P. Kočovský, Chem. Eur. J. 2000, 6, 4348-4357.
29. A. Marchetti, PhD Thesis, Università degli Studi di Pavia, Italy, 2002.
30. S.-F. Zhu, Y. Yang, L.-X. Wang, B. Liu, Q.-L. Zhou, Org. Lett. 2005, 7, 2333-2335.
31. G. Zanoni, F. Castronovo, M. Franzini, G. Vidari, E. Giannini, Chem. Soc. Rev. 2003, 32, 115-129.
32. C. D. Hopkins, L. Guan, H. C. Malinakova, J. Org. Chem. 2005, 70, 6848-6862.