Acid-catalyzed ortho-alkylation of anilines with styrenes: An improved route to chiral anilines with bulky substituents

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5135-5137

  Cherian, Anna E ^a   Domski, Gregory J ^a   Rose, Jeffrey M ^a   Lobkovsky, Emil B ^a   Coates, Geoffrey W ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28244486844     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051916j     Document Type: Article

References (21)

1. (a) Herrmann, W. A.; Cornils, B. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, 2002.
2. (b) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes, 2nd ed.; Wiley & Sons: New York, 1992.
3. Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691-1693.
4. Coates, G. W. Chem. Rev. 2000, 100, 1223-1252.
5. Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283-315.
6. (a) Pellechia, C.; Zambelli, A.; Oliva, L.; Pappalardo, D. Macromolecules 1996, 29, 6990-6993.
7. (b) McClain, S. J.; Feldman, J.; McCord, E. F.; Gardner, K. H.; Teasley, M. F.; Coughlin, E. B.; Sweetman, K. J.; Johnson, L. K.; Brookhart, M. Macromolecules 1998, 31, 6705-6707.
8. (c) Nozaki, K.; Hiyama, T. J. Organomet. Chem. 1999, 576, 248-253.
9. (d) Small, B. L.; Brookhart, M. Macromolecules 1999, 32, 2120-2130.
10. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; John Wiley & Sons: New York, 1992; p 536.
11. Arienti, A.; Bigi, F.; Maggi, R.; Marzi, E.; Moggi, P.; Rastelli, M.; Sartori, R.; Tarantola, F. Tetrahedron 1997, 53, 3795-3804.
12. Cherian, A. E.; Lobkovsky, E. B.; Coates, G. W. Chem. Commun. 2003, 20, 2566-2567.
13. Hart, H.; Kosak, J. R. J. Org. Chem. 1962, 27, 116-121.
14. Anderson, L. L.; Arnold, J.; Bergman, R. G. J. Am. Chem. Soc. 2005, 127, ASAP.
15. Olifirov, D. I.; Koschii, V. A.; Kozlikovskii, Y. B. Zh. Org. Khim. 1992, 28, 1206-1212.
16. 4-catalyzed alkylation of an activated aniline (p-anisidine) with styrene.
17. Uchimaru, Y. Chem. Commun. 1999, 1133-1134.
18. 9 and reduction of 2,1-benzothiazines. Harmata, M.; Kahraman, M. Synthesis 1994, 142-144.
19. 3H, see: Burgoyne, W. F.; Dixon, D. D. Appl. Catal. 1990, 63, 117-127.
20. Flack, H. D.; Bernardinelli, G. J. Appl. Crystallogr. 2000, 33, 1143-1148.
21. Cherian, A. E., Rose, J. M., Lobkovsky, E. B., Coates, G. W. J. Am. Chem. Soc. 2005, 127, 13770-13771.