Simultaneous coordination and double activation phenomena of carbonyl and epoxy oxygen by bis-titanium reagent as a bidentate lewis acid catalyst

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3729-3732

  Asao, Naoki ^a   Kii, Satoshi ^a   Hanawa, Hideo ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE DERIVATIVE; CARBONYL DERIVATIVE; COORDINATION COMPOUND; CYCLOHEXANE DERIVATIVE; EPOXIDE; N,N DIMETHYLFORMAMIDE; REAGENT; TITANIUM DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; STEREOCHEMISTRY;

EID: 0032575170     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00571-1     Document Type: Article

References (35)

1. 1. Reviews: 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;
2. b) Santelli, M.; Pons, J.-M. "Lewis Acids and Selectivity in Organic Synthesis"; CRC Press: Boca Raton, 1995.
3. 2. a) Harman, W. D.; Fairlie, D. P.; Taube, H. J. Am. Chem. Soc., 1986, 108, 8223;
4. b) Huang, Y.-H.; Gladysz, J. J. Chem. Educ., 1988, 65, 298;
5. c) Klein, D. P.; Dalton, D. M.; Mendez, N. Q.; Arif, A. M.; Gladysz, J. J. Organomet. Chem., 1991, 412, C7.
6. 3. Recent bidentate B and A1 complexes: a) Reilly, M.; Oh, T. Tetrahedron Lett. 1994, 35, 7209;
7. b) Reilly, M.; Oh, T. ibid. 1995, 36, 217;
8. c) Reilly, M.; Oh, T. ibid. 1995, 36, 221;
9. d) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307;
10. e) Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett., 1997, 38, 7403. For the intramolecular version of a bidentate aluminum Lewis acid: Sharma, V.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1992, 114, 7931. See also: Galeffi, B.; Simard, M.; Wuest, J. D. Inorg. Chem., 1990, 29, 955.
11. e) Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett., 1997, 38, 7403. For the intramolecular version of a bidentate aluminum Lewis acid: Sharma, V.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1992, 114, 7931. See also: Galeffi, B.; Simard, M.; Wuest, J. D. Inorg. Chem., 1990, 29, 955.
12. e) Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett., 1997, 38, 7403. For the intramolecular version of a bidentate aluminum Lewis acid: Sharma, V.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1992, 114, 7931. See also: Galeffi, B.; Simard, M.; Wuest, J. D. Inorg. Chem., 1990, 29, 955.
13. 4. Theoretical study of formaldehyde/borane (1:2) complex: Lepage, T. J.; Wiberg, K. B. J. Am. Chem. Soc. 1988, 110, 6642.
14. 5. Bidentate transition-metal/carbonyl complexes: a) Adams, H.; Bailey, N. A.; Gauntlett, J. T.; Winter, M. J. J. Chem. Soc., Chem. Commun. 1984, 1360;
15. b) BBeauchamp, A. L.; Olivier, M. J.; Wuest, J. D.; Zacharie, B. J. Am. Chem. Soc. 1986, 108, 73;
16. c) Erker, G; Dorf, U.; Czisch, P; Petersen, J. L. Organometallics 1986, 5, 668;
17. d) Waymouth, R. W.; Potter, K. S.; Schaefer, W. P.; Grubbs, R. H. ibid. 1990, 9, 2843;
18. e) Adams, R. D.; Chen, G.; Chen, L.; Wu, W.; Yin, J. J. Am. Chem. Soc. 1991, 113, 9406;
19. f) Viet, M. T. P.; Shrama, V.; Wuest, J. D. Inorg. Chem. 1991, 30, 3026;
20. g) Bachand, B.; Wuest, J. D. Organometallics 1991, 10, 2015;
21. h) Simard, M.; Vaugeois, J.; Wuest, J. D. J. Am. Chem. Soc. 1993, 115, 370.
22. 6. Reviews on the synthetic utility of Ti reagents: a) Seebach, D.; Weidmann, B.; Widler, L. In "Modern Synthetic Methods", Scheffold, R. Ed.; Salle: Frankfurt, 1983; Vol. 3, p. 217;
23. b) Reetz, M. T. "Organotitanium Reagents in Organic Synthesis"; Springer Verlag: Berlin, 1986;
24. c) Narasaka, K. Synthesis 1991, 1;
25. d) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021;
26. e) Hoveyda, A. H.; Morken, J. P. Angew. Chem. Int. Ed. Engl. 1996, 35, 1263.
27. 7. In the early stage of this study, 2,7-dimethyl-1,8-biphenylenediol was utilized as a spacer for a new bis-titanium reagent based on our previous observation on a bidentate aluminum reagent (see ref 3d). However, the resulting (2,7-dimethyl-1,8-biphenylenedioxy)bis(triisopropoxytitanium) gave only disappointing results in the ketone reduction and allylation of aldehydes.
28. 13C NMR was also observed in the parent 1,8-dihydroxy-and 1-hydroxyanthraquinone: δ 193.19 and 181.74 (activated and non-activated C=O of 1,8-dihydroxyanthraquinone): δ 188.84 and 182.57 (activatedand non-activated C=O of 1-hydroxyanthraquinone) compared to anthraquinone carbonyl (δ 183.34).
29. 4 complex has a symmetric structure like 1.
30. 13C NMR analysis (see text).
31. 4 and the ligand 5 in 1:2 ratio like complex 2. (formula presented)
32. 3SnH. Moreover, the known penta-coordinated Ti complex 7 also exhibited the low reactivity (<1%) in the same reaction (See ref 13).
33. 4 with acetylacetone or ethyl acetoacetate, see: Yamamoto, A.; Kambara, S. J. Am. Chem. Soc. 1957, 79, 4344.
34. 14. Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147.
35. 4 as an external standard gave only one signal (δ -848.64). These results suggest that the 1-DMF complex has a structure like E.