Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines

Angewandte Chemie - International Edition

Volumn 43, Issue 45, 2004, Pages 6125-6128

  Hayashi, Tamio ^a   Kawai, Masahiro ^a   Tokunaga, Norihito ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Amines; Arylation; Asymmetric catalysis; Rhodium titanium

Indexed keywords

CATALYSIS; RHODIUM; SYNTHESIS (CHEMICAL); TITANIUM;

ARENE SULFONAMIDE MOIETY; DIARYLMETHYL AMINES; ENANTIOSELECTIVITY;

AMINES;

AMINE; IMINE; POLYCYCLIC AROMATIC HYDROCARBON; RHODIUM; SULFONAMIDE; TITANIUM;

ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

CATALYSIS; DIMETHYLAMINES; HYDROCARBONS, AROMATIC; IMINES; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; RHODIUM; TITANIUM;

EID: 10044235122     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461338     Document Type: Article

References (35)

1. For examples, see: a) M. J. Bishop, R. W. McNutt, Bioorg. Med. Chem. Lett. 1995, 5, 1311;
2. b) C. M. Spencer, D. Foulds, D. H. Peters, Drugs 1993, 46, 1055;
3. c) S. Sakurai, N. Ogawa, T. Suzuki, K. Kato, T. Ohashi, S. Yasuda, H. Kato, Y. Ito, Chem. Pharm. Bull. 1996, 44, 765.
4. For examples of asymmetric synthesis of diarylmethyl amines, see: a) K. Tomioka, I. Inoue, M. Shindo, K. Koga, Tetrahedron Lett. 1990, 31, 6681;
5. b) L. N. Pridgen, M. K. Mokhallalati, M. J. Wu, J. Org. Chem. 1992, 57, 1237;
6. c) E. J. Corey, C. J. Helal, Tetrahedron Lett. 1996, 37, 4837;
7. d) D. Delorme, C. Berthelette, R. Lavoie, E. Roberts, Tetrahedron: Asymmetry 1998, 9, 3963;
8. e) D. Taniyama, M. Hasegawa, K. Tomioka, Tetrahedron Lett. 2000, 41, 5533;
9. f) D. A. Pflum, D. Krishnamurthy, Z. Han, S. A. Wald, C. H. Senanayake, Tetrahedron Lett. 2002, 43, 923;
10. g) N. Plobeck, D. Powell, Tetrahedron: Asymmetry 2002, 13, 303;
11. h) Z. Han, D. Krishnamurthy, P. Grover, Q. K. Fang, D. A. Pflum, C. H. Senanayake, Tetrahedron Lett. 2003, 44, 4195;
12. i) N. Cabello, J.-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639.
13. For a recent pertinent review on catalytic enantioselective addition to imines, see: S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069.
14. For a Review on catalytic asymmetric arylations, see: C. Bolm, J. P. Hildebrand, K. Muniz, N. Hermanns, Angew. Chem. 2001, 113, 3382; Angew. Chem. Int. Ed. 2001, 40, 3284.
15. For a Review on catalytic asymmetric arylations, see: C. Bolm, J. P. Hildebrand, K. Muniz, N. Hermanns, Angew. Chem. 2001, 113, 3382; Angew. Chem. Int. Ed. 2001, 40, 3284.
16. T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976.
17. N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. 2002, 114, 3844; Angew. Chem. Int. Ed. 2002, 42, 3692.
18. N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. 2002, 114, 3844; Angew. Chem. Int. Ed. 2002, 42, 3692.
19. M. Kuriyama, T. Soeta, X. Hao, Q. Chen, K. Tomioka, J. Am. Chem. Soc. 2004, 126, 8128.
20. For reviews, see: a) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829;
21. b) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169.
22. a) T. Hayashi, N. Tokunaga, K. Yoshida, J. W. Han, J. Am. Chem. Soc. 2002, 124, 12102;
23. see also: b) K. Yoshida, T. Hayashi, J. Am. Chem. Soc. 2003, 125, 2872;
24. c) N. Tokunaga, K. Yoshida, T. Hayashi, Proc. Natl. Acad. Sci. USA 2004, 101, 5445.
25. B. Weidmann, L. Widler, A. G. Olivero, C. D. Maycock, D. Seebach, Helv. Chim. Acta 1981, 64, 357.
26. B. E. Love, P. S. Raje, T. C. Williams II, Synlett 1994, 493.
27. X. Zhang, K. Mashima, K. Koyano, N. Sayo, H. Kumobayashi, S. Akutagawa, H. Takaya, Tetrahedron Lett. 1991, 32, 7283.
28. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal 2001, 343, 264.
29. H. Takaya, S. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629.
30. Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, J. Am. Chem. Soc. 1998, 120, 5579.
31. Y. Takaya, T. Senda, H. Kurushima, M. Ogasawara, T. Hayashi, Tetrahedron: Asymmetry 1999, 10, 4047.
32. T. Hayashi, T. Senda, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 1999, 121, 11591.
33. For the insertion of an imine into an aryl-rhodium bond to form an amido complex, see: C. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 2694.
34. For the deprotection of a 2,4,6-triisopropylbenzenesulfonamide with lithium and DBB in THF, see: C. E. Neipp, J. M. Humphrey, S. F. Martin, J. Org. Chem. 2001, 66, 531.
35. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley, New York, 1999, p. 604.