A ligand-library approach to the highly efficient rhodium/phosphoramidite- catalyzed asymmetric arylation of N,N-dimethylsulfamoyl-protected aldimines

Angewandte Chemie - International Edition

Volumn 45, Issue 17, 2006, Pages 2789-2791

  Jagt, Richard B C ^a   Toullec, Patrick Y ^a   Geerdink, Danny ^a   De Vries, Johannes G ^a   Feringa, Ben L ^a   Minnaard, Adriaan J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Arylation; Arylboronic acids; Asymmetric catalysis; Diarylmethylamines; Phosphoramidites

Indexed keywords

ARYLATION; ARYLBORONIC ACIDS; ASYMMETRIC CATALYSIS; DIARYLMETHYLAMINES; PHOSPHORAMIDITES;

AMINES; CATALYSIS; CATALYSTS; INORGANIC ACIDS; MICROWAVES; REACTION KINETICS;

RHODIUM COMPOUNDS;

BORONIC ACID DERIVATIVE; LIGAND; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDOUS ACID; RHODIUM; SESQUITERPENE; SULFUR;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; STEREOISOMERISM;

BORONIC ACIDS; CATALYSIS; LIGANDS; METHYLATION; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; RHODIUM; SESQUITERPENES; STEREOISOMERISM; SULFUR;

EID: 33745577878     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504309     Document Type: Article

References (47)

1. For examples of such pharmacophores, see: a) N. Plobeck, D. Delorme, Z.-Y. Wei, H. Yang, F. Zhou, P. Schwarz, L. Gawell, H. Gagnon, B. Pelcman, R. Schmidt, S.-Y. Sue, C. Walpole, W. Brown, E. Zhou, M. Labarre, K. Payza, S. St-Onge, A. Kamassah, P.-E. Morin, D. Projean, J. Med. Chem. 2000, 43, 3878;
2. b) C. J. Opalka, T. E. D'Ambra, J. J. Faccone, G. Bodxon, E. Cossement, Synthesis 1995, 766.
3. a) E. J. Corey, C. J. Helal, Tetrahedron Lett. 1996, 37, 4837;
4. b) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. 2002, 114, 3844;
5. Angew. Chem. Int. Ed. 2002, 41, 3692;
6. c) N. Cabello, J.-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639.
7. For a review on catalytic enantioselective addition to imines, see: a) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069;
8. for a review on catalytic asymmetric arylations, see: b) C. Bolm, J. P. Hildebrand, K. Muniz, N. Hermanns, Angew. Chem. 2001, 113, 3382;
9. Angew. Chem. Int. Ed. 2001, 40, 3284;
10. for a review on rhodium-catalyzed carbon - carbon-bond-forming reactions, see: c) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 169;
11. d) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169;
12. e) Modern Rhodium-Catalyzed Organic Reactions (Ed.: P. A. Evans), Wiley-VCH, Weinheim, 2005.
13. a) T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976;
14. b) M. Ueda, N. Miyaura, J. Organomet. Chem. 2000, 595, 31.
15. T. Hayashi, M. Kawai, N. Tokunaga, Angew. Chem. 2004, 116, 6251;
16. Angew. Chem. Int. Ed. 2004, 43, 6125.
17. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
18. For the first non-enantioselective addition of arylboronic acids to imines, see reference [4b] and: M. Ueda, A. Saito, N. Miyaura, Synlett 2000, 11, 1637.
19. M. Kuriyama, T. Soeta, X. Hao, Q. Chen, K. Tomioka, J. Am. Chem. Soc. 2004, 126, 8128.
20. a) N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 13 584;
21. b) Y. Otomaru, N. Tokunaga, R. Shintani, T. Hayashi, Org. Lett. 2005, 7, 307.
22. D. J. Weix, Y. Shi, J. A. Ellman, J. Am. Chem. Soc. 2005, 127, 1092. The authors of this paper also mention the problematic removal of the N-tosyl activating/protecting group and use the N-diphenylphosphinoyl group as an alternative.
23. For difficulties concerning the removal of the N-tosyl protecting group in this system, see reference [9], R. R. Milburn, V. Snieckus, Angew. Chem. 2004, 116, 910;
24. Angew. Chem. Int. Ed. 2004, 43, 892, and references therein.
25. For the synthesis of N,N-dimethylsulfamoyl-protected benzaldimines, see: a) M. Huisman, R. ten Have, A. M. van Leusen, Synth. Commun. 1997, 27, 945;
26. b) R. ten Have, M. Huisman, A. Meetsma, A. M. van Leusen, Tetrahedron 1997, 53, 11 355.
27. B. L. Feringa, Acc. Chem. Res. 2000, 33, 346.
28. a) J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681;
29. see also: J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 1385;
30. b) J.-G. Boiteau, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2003, 68, 9481;
31. c) A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 3111;
32. d) R. B. C. Jagt, J. G. de Vries, B. L. Feringa, A. J. Minnaard, Org. Lett. 2005, 7, 2433.
33. a) L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, Org. Lett. 2004, 6, 1733;
34. b) A. Duursma, L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, A. J. Minnaard, B. L. Feringa, Org. Biomol. Chem. 2004, 2, 1682.
35. B. E. Love, P. S. Raje, T. C. Williams, Synlett 1994, 493.
36. a) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475;
37. Angew. Chem. Int. Ed. 1998, 37, 3279;
38. b) C. Moreau, C. Hague, A. S. Weller, C. G. Frost, Tetrahedron Lett. 2001, 42, 6957.
39. T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052.
40. For a previous example of 1,2-addition to benzaldimines in aprotic media, see reference [10].
41. a) L. V. Kudzma, S. P. Turnbull, Synthesis 1991, 1021;
42. b) J. Hine, H.-M. Tsay, J. Org. Chem. 1983, 48, 3797;
43. c) R. Adams, W. P. Samuels, J. Am. Chem. Soc. 1955, 77, 5375.
44. For references concerning transamination reactions of sulfamide and derivatives thereof, see: a) S. D. McDermott, W. J. Spillane, Synthesis 1983, 192;
45. b) M. Preiss, Chem. Ber. 1978, 111, 1915.
46. C. O. Kappe, Angew. Chem. 2004, 116, 6408;
47. Angew. Chem. Int. Ed. 2004, 43, 6250.