Bis-zirconium and bis-hafnium catalysts for the strong activation of carbonyl substrates
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Published:2000-07
Issue:29
Volume:41
Page:5543-5546
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ISSN:0040-4039
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Container-title:Tetrahedron Letters
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language:en
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Short-container-title:Tetrahedron Letters
Author:
Hanawa Hideo,Kii Satoshi,Asao Naoki,Maruoka Keiji
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference8 articles.
1. Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. For similar bidentate Lewis acid chemistry, see: (a) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307. (b) Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403. (c) Asao, N.; Liu, P.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2507. (d) Ooi, T.; Saito, A.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3745. (e) Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 2347. 2. Lewis acid chemistry, see: (a) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1.10, p. 283. 3. (b) Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1995. 4. In the synthesis of a mono-Zr reagent, 2 equiv. of 3-t-butyl-2-hydroxy-5-methylbenzophenone is incorporated, whether 0.5 or 1 equiv. of Zr(OPri)4·PriOH is present, to furnish fully-coordinated 3 as a sole product, which still has a coordination ability toward carbonyl substrates by ligand exchange as ascertained by 13C NMR analysis. For similar argument, see Ref 1. 5. Asymmetric stoichiometric allylations: Allenylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (b) Short, R. P.; Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401. Allylboronates: (d) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (e) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walts, A. E.; Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R.; Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.; Park, J. C. J. Org. Chem. 1990, 55, 4109. See also: (i) Reetz, M. T.; Zierke, T. Chem. Ind. 1988, 663. Allylboradiazolidines: (j) Corey, E. J.; Yu, C.-M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495. Allyltitanates: (k) Riediker, M.; Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1989, 28, 494. (l) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (m) Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. Allylaluminum derivatives: (n) Minowa, N.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1987, 60, 3697. Allylstannanes: (o) Otera, J.; Kawasaki, Y.; Mizuno, H.; Shimizu, Y. Chem. Lett. 1983, 1529. (p) Otera, J.; Yoshinaga, Y.; Yamaji, T.; Yoshioka, T.; Kawasaki, Y. Organometallics 1985, 4, 1213. (q) Boldrini, G. P.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1986, 685. (r) Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. (s) Boga, C.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Organomet. Chem. 1988, 353, 177.
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