Asymmetric Dihydroxylation with MeO-Polyethyleneglycol-Bound Ligands

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 7, 1997, Pages 741-743

  Bolm, Carsten ^a   Gerlach, Arne ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Dihydroxylations; Homogeneous catalysis

Indexed keywords

EID: 0030854968     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199707411     Document Type: Article

References (38)

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15. A recently described polymer-bound phthalazine alkaloid yields excellent enantioselectivities (>99% ee) in the AD of stilbene and methyl cinnamate: C. E. Song, J. W. Yang, H. J. Ha, S. Lee, Tetrahedron: Asymmetry 1996, 7, 645.
16. a) H. Han, K. D. Janda, J. Am. Chem. Soc. 1996, 118, 7632;
17. b) see also S. Borman, Chem. Eng. News 1996, August 26, p. 36.
18. This concept has previously been used in other catalyses: c) E. Bayer, V. Schuring, Angew. Chem. 1975, 87, 484; Angew. Chem. Int. Ed. Engl. 1975, 14, 493; d) E. Bayer, V. Schurig, Chemtech, 1976, 6, 212; e) M. P. Doyle, M. Y. Eismont, D. E. Bergbreiter, H. N. Gray, J. Org. Chem. 1992, 57, 6103, and references therein.
19. This concept has previously been used in other catalyses: c) E. Bayer, V. Schuring, Angew. Chem. 1975, 87, 484; Angew. Chem. Int. Ed. Engl. 1975, 14, 493; d) E. Bayer, V. Schurig, Chemtech, 1976, 6, 212; e) M. P. Doyle, M. Y. Eismont, D. E. Bergbreiter, H. N. Gray, J. Org. Chem. 1992, 57, 6103, and references therein.
20. This concept has previously been used in other catalyses: c) E. Bayer, V. Schuring, Angew. Chem. 1975, 87, 484; Angew. Chem. Int. Ed. Engl. 1975, 14, 493; d) E. Bayer, V. Schurig, Chemtech, 1976, 6, 212; e) M. P. Doyle, M. Y. Eismont, D. E. Bergbreiter, H. N. Gray, J. Org. Chem. 1992, 57, 6103, and references therein.
21. This concept has previously been used in other catalyses: c) E. Bayer, V. Schuring, Angew. Chem. 1975, 87, 484; Angew. Chem. Int. Ed. Engl. 1975, 14, 493; d) E. Bayer, V. Schurig, Chemtech, 1976, 6, 212; e) M. P. Doyle, M. Y. Eismont, D. E. Bergbreiter, H. N. Gray, J. Org. Chem. 1992, 57, 6103, and references therein.
22. a) J. M. Harris, Poly(Ethylene Glycol) Chemistry, Plenum, New York, 1992;
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24. c) M. L. Nucci, R. Shorr, A. Abuchowski, Adv. Drug Del. Rev. 1991, 6, 133;
25. d) N. V. Katre, ibid. 1993, 10, 91.
26. Janda and coworkers have used MeO-PEG for the combinatorial synthesis of small molecules and compound libraries: a) H. Han, M. M. Wolfe, S. Brenner, K. D. Janda, Proc. Natl. Acad. Sci. USA 1995, 92, 6419; b) H. Han, K. D. Janda, J. Am. Chem. Soc. 1996, 118, 2539.
27. Janda and coworkers have used MeO-PEG for the combinatorial synthesis of small molecules and compound libraries: a) H. Han, M. M. Wolfe, S. Brenner, K. D. Janda, Proc. Natl. Acad. Sci. USA 1995, 92, 6419; b) H. Han, K. D. Janda, J. Am. Chem. Soc. 1996, 118, 2539.
28. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
29. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
30. 2-PHAL ligand that apparently gives higher enantioselectivities is mentioned in a footnote in ref. [6a], but not specified in more detail.
31. DHQ = dihydroquinine; DHQD = dihydroquinidine.
32. 2PYR]: G. A. Crispino, K.-S. Jeong, H. C. Kolb, Z.-M. Wang, D. Xu, K. B. Sharpless, J. Org. Chem. 1993, 58, 3785.
33. r = 5000; number of hydroxy groups OHN = 0.2 mass equiv per gram).
34. Aryl dibromide 8 was prepared from pyrazine-2,3-dicarboxylic acid in analogy to the corresponding nonhalogenated compound (ref. [3b]).
35. The ee values with N-methylmorpholine oxide (NMO) are comparably lower: stilbene 99% ee, styrene 81% ee, 1-methylstyrene 78% ee.
36. 3}. Other MeO-PEG attachments are currently under investigation.
37. For experimental details see procedure in ref. [12].
38. Column material: Daicel, Chiralcel, Entry 1: bis-MTPA-ester (OD), 2: diol (OB); 3: bisbenzoate (OD); 4: bis-p-methoxybenzoate (OD), 5: tert-butyl-diphenylsilyl monoether (OD).