Catalytic asymmetric desymmetrization of meso-diamide derivatives through enantioselective N-allylation with a chiral π-allyl Pd catalyst: Improvement and reversal of the enantioselectivity

Journal of Organic Chemistry

Volumn 71, Issue 6, 2006, Pages 2524-2527

  Kitagawa, Osamu ^a   Matsuo, Shinichi ^a   Yotsumoto, Kanako ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC DESYMMETRIZATION PRODUCTS; BISTOLUNESULFONYLAMIDE; CATALYTIC ASYMMETRIC DESYMMETRIZATION; ENANTIOSELECTIVE N-ALLYLATION; MESO-DIAMIDE; SULFONYLAMIDES; TROST LIGANDS-PD CATALYSTS;

AMINES; CATALYSTS; DERIVATIVES; ORGANIC COMPOUNDS;

NITROGEN COMPOUNDS;

BIS(2,4,6 TRIISOPROPYLBENZENE)SULFONYLAMIDE; BISTOLUENESULFONYLAMIDE DERIVATIVE; DIAMIDE; DIAMINE DERIVATIVE; LIGAND; PALLADIUM; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CONFORMATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

ALKYLATION; ALLYL COMPOUNDS; CATALYSIS; DIAMIDE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 33645028620     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052488y     Document Type: Article

References (41)

1. (a) Michalson, E. T.; Szmuszkovicz, J. Prog. Drug Res. 1989, 33, 135.
2. (b) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
3. (a) Li, Z.; Fernández, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611.
4. (b) Yamada, K.; Moll, G.; Shibasaki, M. Synlett 2001, 980.
5. (c) Ooi, T.; Sakai, D.; Takeuchi, M.; Tayama, E.; Maruoka, K. Angew. Chem., Int. Ed. 2003, 42, 5868.
6. (d) Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836.
7. (e) Chune, D.; Alper, H. Tetrahedron: Asymmetry 2004, 15, 1537.
8. (a) Radesca, L.; Bowen, W. D.; Paolo, L. D.; De Costa, B. R. J. Med. Chem. 1991, 34, 3058.
9. (b) De Costa, B. R.; Dominguez, C.; He, X.; Williams, W.; Radesca, L.; Bowen, W. J. Med. Chem. 1992, 35, 4334.
10. (c) Novakova, M.; Ela, C.; Bowen, W. D.; Hasin, Y.; Eilam, Y. Eur. J. Pharmacol. 1998, 353, 315.
11. (d) Hong, W.; Werling, L. L. Eur. J. Pharmacol. 2002, 436, 35.
12. (e) Govindaraju, T.; Gonnade, R. G.; Bhadbhade, M. M.; Kumar, V. A.; Ganesh, K. N. Org. Lett. 2003, 5, 3013.
13. (f) Govindaraju, T.; Kumar, V. A.; Ganesh, K. N. J. Org. Chem. 2004, 69, 5725.
14. (g) Govindaraju, T.; Kumar, V. A.; Ganesh, K. N. J. Am. Chem. Soc. 2005, 127, 4144.
15. Kitagawa, O.; Yotsumoto, K.; Kohriyama, M.; Dobashi, Y.; Taguchi, T. Org. Lett. 2004, 6, 3605.
16. For reviews on catalytic asymmetric allylation with a chiral π-allylpalladium complex see: (a) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1994; pp 325-365.
17. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
18. To the best of our knowledge, there has been no report on asymmetric desymmetrization of meso-diamine derivatives. In the reaction with diamine substrates, the enantiocontrol may be difficult because of high nucleophilicity of the amino group and the strong ability to chelate with transition metal, which may result in dissociation of the chiral ligand from the catalytic center and deactivation of the catalyst.
19. In contrast to diamine derivatives, catalytic asymmetric desymmetrization of meso-diols has been well-known, (a) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430.
20. (b) Oriyama, T.; Imai, K.; Sano, T.; Hosoya, T. Tetrahedron Lett. 1998, 39, 397.
21. (c) Kawabata, T.; Stragies, R.; Fukuya, T.; Nagaoka, Y.; Schedel, H.; Fuji, K. Tetrahedron Lett. 2003, 44, 1545.
22. (d) Matsumura, Y.; Maki, T.; Murakami, S.; Onomura, O. J. Am. Chem. Soc. 2003, 125, 2052.
23. (e) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410.
24. (f) Shimizu, H.; Katsuki, T. Chem. Lett. 2003, 32, 480.
25. (g) Mizuta, S.; Sadamori, M.; Fujimoto, T.; Yamamoto, I. Angew. Chem., Int. Ed. 2003, 42, 3383.
26. (h) Mandal, S. K.; Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Org. Chem. 2003, 68, 4600.
27. (i) Mizuta, S.; Tsuzuki, T.; Fujimoto, T.; Yamamoto, I. Org. Lett. 2005, 7, 3633.
28. (j) For a review see: Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
29. (a) Kitagawa, O.; Kohriyama, M.; Taguchi, T. J. Org. Chem. 2002, 67, 8682.
30. (b) Terauchi, J.; Curran, D. P. Tetrahedron: Asymmetry 2003, 14, 587.
31. (c) Kitagawa, O.; Takahashi, M.; Yoshikawa, M.; Taguchi, T. J. Am. Chem. Soc. 2005, 127, 3676.
32. (a) Trost, B. M.; Vranken, D. L. V.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327.
33. (b) Trost, B. M.; Schroeder, G. M.; Kristensen, J. Angew. Chem., Int. Ed. 2002, 41, 3492.
34. Neipp, C. E.; Humphrey, J. M.; Martin, S. F. J. Org. Chem. 2001, 66, 531.
35. For recent examples in relation to the switch of enantioselectivity by the use of the same chiral ligand, see: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.
36. (b) Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220.
37. (c) Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908.
38. (d) Wilkinson, J. A.; Rossington, S. B.; Leonard, J.; Hussein, N. Tetrahedron Lett. 2004, 45, 1191.
39. (e) Du, D.; Lu, S.; Fang, T.; Xu, J. J. Org. Chem. 2005, 70, 3712.
40. (f) Desimoni, G.; Faita, G.; Guala, M.; Laurenti, A.; Mella, M. Chem. Eur. J. 2005, 11, 3816.
41. The reaction conditions in the conversion of Schemes 1 and 3 were not optimized, while as described in our previous paper,4 similar conversion with trisyl derivative 2a gave 4f in 46% yield.