Highly enantioselective hydrovinylation of α-alkyl vinylarenes. An approach to the construction of all-carbon quaternary stereocenters

Journal of the American Chemical Society

Volumn 128, Issue 9, 2006, Pages 2780-2781

  Shi, Wen Jian ^a   Zhang, Qi ^a   Xie, Jian Hua ^a   Zhu, Shou Fei ^a   Hou, Guo Hua ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IBUPROFEN; NAPROXEN; TRANSITION ELEMENT; VINYL DERIVATIVE;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; DERIVATIZATION; ENANTIOSELECTIVITY; HECK REACTION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

HYDROCARBONS, AROMATIC; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 33644952259     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja057654y     Document Type: Article

References (28)

1. For reviews, see: (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401.
2. (b) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
3. (c) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
4. (d) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363-6367.
5. For recent examples of highly enantioselective synthesis of chiral compounds containing all-carbon quaternary stereocenters, see: (a) Peterson, E. A.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11943-11948.
6. (b) Wu, J.; Mampreian, D. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4584-4585.
7. (c) Mermerian, A. H.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 5604-5607.
8. (d) Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 62-63.
9. (e) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105-108.
10. (f) Augustin, M. D.; Palais, L.; Alexakis, A. Angew. Chem., Int. Ed. 2005, 44, 1376-1378.
11. For reviews, see: (a) Jolly, P. W.; Wilke, G. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: New York, 1996; Vol 2, p 1024 and references therein.
12. (b) Goossen, L. J. Angew. Chem., Int. Ed. 2002, 41, 3775-3778.
13. (c) RajanBabu, T. V. Chem. Rev. 2003, 103, 2845-2860.
14. (a) Wilke, G.; Monkiewicz, J. DOS 3 618 169, priority 30.05.1986; Chem. Abstr. 1988, 109, P6735.
15. (b) Wilke, G. Angew. Chem., Int. Ed. 1988, 27, 185.
16. (a) Nomura, N.; Jin, J.; Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 459-460.
17. (b) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734-735.
18. (c) RajanBabu, T. V.; Nomura, N.; Jin, J.; Nandi, M.; Park, H.; Sun, X. J. Org. Chem. 2003, 68, 8431-8446.
19. (d) Park, H.; Kumareswaran, R.; RajanBabu, T. V. Tetrahedron 2005, 61, 6352-6367.
20. (a) Franciò, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737.
21. (b) Hölscher, M.; Franciò, G.; Leitner, W. Organometallics 2004, 23, 5606.
22. For nonenantioselective hydrovinylation of α-methylstyrene, see refs 3a, 5c, and (a) Monteiro, A. L.; Seferin, M.; Dupont, J.; Souza, R. F. Tetrahedron Lett. 1996, 37, 1157-1160.
23. (b) Fassina, V.; Ramminger, C.; Seferin, M.; Monteiro, A. L. Tetrahedron 2000, 56, 7403-7409.
24. Shi, W.-J.; Xie, J.-H.; Zhou, Q.-L. Tetrahedron: Asymmetry 2005, 3, 705-710.
25. (a) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480-481.
26. (b) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348-2349.
27. (a) Zhang, W.; Wang, L.-X.; Shi, W.-J.; Zhou, Q.-L. J. Org. Chem. 2005, 70, 3734-3736.
28. (b) Zhu, S.-F.; Yang, Y.; Wang, L.-X.; Liu, B.; Zhou, Q.-L. Org. Lett. 2005, 7, 2333-2335.