Enantioselective palladium-catalyzed decarboxylative allylic alkylations

Angewandte Chemie - International Edition

Volumn 45, Issue 32, 2006, Pages 5246-5248

  You, Shu Li ^a   Dai, Li Xin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allylic alkylation; Asymmetric catalysis; Enols; Ketones; Palladium

Indexed keywords

ALKYLATION; CATALYSIS; KETONES; STEREOCHEMISTRY;

ALLYLIC ALKYLATION; ASYMMETRIC CATALYSIS; ENANTIOENRICHED KETONES; ENOLS;

PALLADIUM;

EID: 33747879509     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601889     Document Type: Short Survey

References (21)

1. Reviews: a) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422;
2. b) B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705;
3. c) B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943;
4. d) J. A. Tunge, E. C. Burger, Eur. J. Org. Chem. 2005, 9, 1715-1726.
5. a) I. Shimizu, T. Yamada, J. Tsuji, Tetrahedron Lett. 1980, 21, 3199-3202;
6. b) J. Tsuji, I. Minami, I. Shimizu, Tetrahedron Lett. 1983, 24, 1793-1796;
7. c) J. Tsuji, T. Yamada, I. Minami, M. Yuhara, M. Nisar, I. Shimizu, J. Org. Chem. 1987, 52, 2988-2995;
8. d) J. Tsuji, I. Minami, Acc. Chem. Res. 1987, 20, 140-145;
9. e) I. Shimizu, H. Ishii, A. Tasaka, Chem. Lett. 1989, 1127-1128.
10. E. C. Burger, J. A. Tunge, Org. Lett. 2004, 6, 4113-4115.
11. D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 15044-15045.
12. R. Kuwano, N. Ishida, M. Murakami, Chem. Commun. 2005, 3951-3952.
13. B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 2846-2847.
14. B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 17180-17181.
15. J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. 2005, 117, 7084-7087;
16. Angew. Chem. Int. Ed. 2005, 44, 6924-6927.
17. M. Nakamura, A. Hajra, K. Endo, E. Nakamura, Angew. Chem. 2005, 117, 7414-7417;
18. Angew. Chem. Int. Ed. 2005, 44, 7248-7251.
19. B. M. Trost, R. N. Bream, J. Xu, Angew. Chem. 2006, 118, 3181-3184;
20. Angew. Chem. Int. Ed. 2006, 45, 3109-3112.
21. After submission of this manuscript, Stoltz and McFadden reported the total synthesis of (+)-dichroanone utilizing a Pd-catalyzed decarboxylative AAA reaction as a key step to install a chiral quaternary carbon center. For details, see: R. M. McFadden, B. M. Stoltz, J. Am. Chem. Soc. 2006, 128, 7738-7739.