Dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate]: A new chiral Rh(II) catalyst for enantioselective amidation of C-H bonds

Tetrahedron Letters

Volumn 43, Issue 52, 2002, Pages 9561-9564

  Yamawaki, Minoru ^a   Tsutsui, Hideyuki ^a   Kitagaki, Shinji ^a   Anada, Masahiro ^a   Hashimoto, Shunichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; CARBON; CHLORINE; DIRHODIUM TETRAKIS(N TETRACHLOROPHTHALOYL TERT LEUCINATE); HYDROGEN; PHTHALIMIDE; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; ATOM; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; STEREOCHEMISTRY;

EID: 0037164672     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02432-2     Document Type: Article

References (53)

1. Breslow R., Gellman S.H. J. Chem. Soc., Chem. Commun. 1982;1400.
2. Breslow R., Gellman S.H. J. Am. Chem. Soc. 105:1983;6728.
3. Mansuy D., Mahy J.-P., Dureault A., Bedi G., Battioni P. J. Chem. Soc., Chem. Commun. 1:1984;1161.
4. Mahy J.-P., Bedi G., Battioni P., Mansuy D. Tetrahedron Lett. 29:1988;1927.
5. For a review of metal-catalyzed nitrene transfer, see: Müller P. Doyle M.P. Advances in Catalytic Processes. 2:1997;113 JAI Press, Greenwich.
6. For reviews, see: (a) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag, Berlin, 1999; Chapter 17; (b) Katsuki, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 6B.4; (c) Faul, M. M.; Evans, D. A. In Asymmetric Oxidation Reactions; Katsuki, T., Ed.; Oxford University Press: New York, 2001; Chapter 2.7.
7. For reviews, see: (a) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag, Berlin, 1999; Chapter 17; (b) Katsuki, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 6B.4; (c) Faul, M. M.; Evans, D. A. In Asymmetric Oxidation Reactions; Katsuki, T., Ed.; Oxford University Press: New York, 2001; Chapter 2.7.
8. For reviews, see: (a) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag, Berlin, 1999; Chapter 17; (b) Katsuki, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 6B.4; (c) Faul, M. M.; Evans, D. A. In Asymmetric Oxidation Reactions; Katsuki, T., Ed.; Oxford University Press: New York, 2001; Chapter 2.7.
9. Evans D.A., Faul M.M., Bilodeau M.T., Anderson B.A., Barnes D.M. J. Am. Chem. Soc. 115:1993;5328.
10. Li Z., Conser K.R., Jacobsen E.N. J. Am. Chem. Soc. 115:1993;5326.
11. Li Z., Quann R.W., Jacobsen E.N. J. Am. Chem. Soc. 117:1995;5889.
12. (a) Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469;
13. (b) Nishikoshi, H.; Katsuki, T. Tetrahedron Lett. 1996, 37, 9245.
14. See also: (c) Minakata, S.; Ando, T.; Nishimura, M.; Ryu, I.; Komatsu, M. Angew. Chem., Int. Ed. 1998, 37, 3392.
15. Lai T.-S., Kwong H.-L., Che C.-M., Peng S.-M. Chem. Commun. 1997;2373.
16. Liang J.-L., Huang J.-S., Yu Z.-Q., Zhu N., Che C.-M. Chem. Eur. J. 8:2002;1563.
17. Nägeli I., Baud C., Bernardinelli G., Jacquier Y., Moran M., Müller P. Helv. Chim. Acta. 80:1997;1087.
18. (a) Zhou, X.-G.; Yu, X.-Q.; Huang, J.-S.; Che, C.-M. Chem. Commun. 1999, 2377;
19. (b) Very recently, they have reported chiral Ru(III)-porphyrine catalyzed enantioselective intramolecular C-H amidation of sulfamate esters with up to 87% ee. Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2002, 41, 3465.
20. Kohmura Y., Katsuki T. Tetrahedron Lett. 42:2001;3339.
21. Hashimoto S., Watanabe N., Anada M., Ikegami S. J. Synth. Org. Chem. Jpn. (in English). 54:1996;988.
22. Kitagaki S., Anada M., Kataoka O., Matsuno K., Umeda C., Watanabe N., Hashimoto S. J. Am. Chem. Soc. 121:1999;1417.
23. Takahashi T., Tsutsui H., Tamura M., Kitagaki S., Nakajima M., Hashimoto S. Chem. Commun. 2001;1604.
24. Kitagaki S., Yanamoto Y., Tsutsui H., Anada M., Nakajima M., Hashimoto S. Tetrahedron Lett. 42:2001;6361.
25. Tsutsui H., Matsuura M., Makino K., Nakamura S., Nakajima M., Kitagaki S., Hashimoto S. Israel J. Chem. 41:2001;283.
26. 4, see: Kitagaki S., Matsuda H., Watanabe N., Hashimoto S. Synlett. 1997;1171.
27. 2 as described: Yamada Y., Yamamoto T., Okawara M. Chem. Lett. 1975;361.
28. 4 afforded the amidation product 3 in 18% yield with 19% ee.
29. 9.
30. R-1-Aminoindan was purchased from Aldrich Chemical Company, Inc.
31. 4-catalyzed C-H amidation of TsN=IPh with 2, which gave the amidation product in 16% yield with 38% ee. On the other hand, a similar reaction of [[(4-methoxyphenyl)sulfonyl]imino]phenyliodinane gave a complex mixture of products.
32. The reason cannot be given at present.
33. Jacobsen E.N., Zhang W., Güler M.L. J. Am. Chem. Soc. 113:1991;6703.
34. RajanBabu T.V., Ayers T.A., Halliday G.A., You K.K., Calabrese J.C. J. Org. Chem. 62:1997;6012.
35. Yan Y.-Y., RajanBabu T.A. Org. Lett. 2:2000;4137.
36. Casalnuovo A.L., RajanBabu T.V., Ayers T.A., Warren T.H. J. Am. Chem. Soc. 116:1994;9869.
37. Schnyder A., Hintermann L., Togni A. Angew. Chem., Int. Ed. Engl. 34:1995;931.
38. Park S.-B., Murata K., Matsumoto H., Nishiyama H. Tetrahedron: Asymmetry. 6:1995;2487.
39. Chen Y., Yekta S., Martyn L.J.P., Zheng J., Yudin A.K. Org. Lett. 2:2000;3433.
40. Ishitani H., Ueno M., Kobayashi S. J. Am. Chem. Soc. 122:2000;8180.
41. The synthesis of the fluorinated analogues of chiral dirhodium(II) carboxamidate complexes and their evaluation have recently been reported by Doyle and co-workers, see: (a) Doyle, M. P.; Hu, W.; Phillips, I. M.; Moody, C. J.; Pepper, A. G.; Slawin, A. M. Z. Adv. Synth. Catal. 2001, 343, 112; (b) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366.
42. The synthesis of the fluorinated analogues of chiral dirhodium(II) carboxamidate complexes and their evaluation have recently been reported by Doyle and co-workers, see: (a) Doyle, M. P.; Hu, W.; Phillips, I. M.; Moody, C. J.; Pepper, A. G.; Slawin, A. M. Z. Adv. Synth. Catal. 2001, 343, 112; (b) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366.
43. Callot H.J., Metz F. Tetrahedron. 41:1985;4495.
44. Hoshino Y., Yamamoto H. J. Am. Chem. Soc. 122:2000;10452.
45. 20 -34.7 (c 1.69, EtOH)] were prepared from (S)-tert-leucine and tetrafluoro- or tetrachlorophthalic anhydride without any racemization.
46. Bose, A. K. Organic Syntheses, Collect. Vol. V; Wiley: New York, 1973; p. 973.
47. 13C NMR), analytical, and mass spectral characteristics.
48. Eisenbraun E.J., Harms W.M., Burnham J.W., Dermer O.C., Laramy R.E., Hamming M.C., Keen G.W., Flanagan P.W. J. Org. Chem. 42:1977;1967.
49. Bogert M.T., Davidson D., Apfelbaum P.M. J. Am. Chem. Soc. 56:1934;959.
50. Weidmann R., Guette J.P. C.R. Seances Acad. Sci., Ser. C. 268:1969;2225.
51. Smith R.A., White R.L., Krantz A. J. Med. Chem. 31:1988;1558.
52. (R)-1-Phenylethylamine was purchased from Wako Chemical Industries, Ltd.
53. 3). Enantiomeric excess was determined to be 70% by HPLC analysis [column, Daicel Chiralpak AD; eluent, 3:1 n-hexane:i-PrOH; flow rate, 1.0 mL/min; retention time, 11.8 min [major (R)-isomer] and 16.7 min [minor (S)-isomer].