Asymmetric catalysis of carbonyl-ene and aldol reactions with fluoral by chiral binaphthol-derived titanium complex

Tetrahedron

Volumn 52, Issue 1, 1996, Pages 85-98

  Mikami, Koichi ^a   Yajima, Tomoko ^a   Takasaki, Tsuyoshi ^a   Matsukawa, Satoru ^a   Terada, Masahiro ^a   Uchimaru, Tadafumi ^b   Maruta, Masamichi ^c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

^c CENTRAL GLASS CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; ORGANOFLUORINE DERIVATIVE;

CONFERENCE PAPER; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029656027     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00862-3     Document Type: Article

References (56)

1. Reviews: Resnati, G. Tetrahedron 1993, 49, 9385.
2. Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, NY, 1990.
3. Liebman, J. F.; Greenberg, A.; Dolbier, Jr., W. R., Eds. Fluorine Containing Molecules; VCH: Deerfield Beach, FL, 1988.
4. Ishikawa, N, Ed. Synthesis and Reactivity of Fluorocompounds; CMC: Tokyo, 1987, Vol. 3.
5. Welch, J. T. Tetrahedron 1987, 43, 3123.
6. Mann, J. Chem. Soc. Rev. 1987, 16, 381.
7. Kitazume, T.; Yamazaki, T. J. Synth. Org. Chem. Jpn. 1987, 45, 888.
8. Ojima, I. L'Actualite Chimique 1987, May, 179.
9. Smart, B. In The Chemistry of Halides, Pseudohalides and Azides; Patai, S.; Rapoport, Z. Eds.; Wiley: New York, NY, 1983, Suppl. D; pp. 603-655.
10. Filler, R.; Kobayashi, Y., Ed. Biomedical Aspects of Fluorine Chemistry; Kodansha Ltd.: Tokyo, 1982.
11. Banks, R. E., Ed. Preparation, Properties and Industrial Applications of Organofluorine Compounds; E. Horwood: Chichester, 1982.
12. Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd Ed.; E. Horwood: Chichester, 1976.
13. Chambers, R. D. Fluorine in Organic Chemistry; Wiley-Interscience: New York, NY, 1973.
14. Ciba Foundation Symposium, Carbon-Fluorine Compounds, Chemistry, Biochemistry and Biological Activities; Elsevier: New York, NY, 1972.
15. (a) Kitazume, T.; Lin, J. T.; Yamazaki, T. Tetrahedron: Asymm. 1991, 2, 235.
16. (b) Scolastico, C.; Conca, E.; Prati, L.; Guanti, G.; Banfi, L.; Berti, A.; Farina, P.; Valcavi, V. Synthesis 1985, 850.
17. Nishiyama, S. et al. 17th Ekisho Toronkai, Abstract 2F315 (1991);
18. Also see: Yoshino, K.; Ozaki, M.; Taniguchi, H.; Ito, M.; Sato, K.; Yamazaki, N.; Kitazume, T. J. Jpn. Appl. Phys. 1987, 26, L77.
19. For our preliminary communications of asymmetric catalytic fluoral-ene reactions: (a) Mikami, K.; Yajima. T.; Terada, M.; Uchimaru, T. Tetrahedron Lett. 1993, 34, 7591.
20. (b) Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymm. 1994, 5, 1087.
21. Asymmetric catalytic fluoral-aldol reactions: (c) Mikami, K.; Takasaki, T.; Matsukawa, S.; Maruta, M. Synlett in press.
22. Most recently asymmetric catalytic aldol reactions with fluorinated aromatic aldehydes and ketones were reported: Soloshonok, V. A.; Hayashi, T. Tetrahedron Lett. 1994, 35, 2713.
23. Soloshonok, V. A.; Hayashi, T. Tetrahedron: Asymm. 1994, 5, 1091.
24. Review: (a) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
25. (b) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255.
26. For asymmetric catalysis of glyoxylate-ene reactions: (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940.
27. (b) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949.
28. (c) Terada, M.; Mikami, K.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1623.
29. (d) Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671.
30. (e) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1992, 71, 14.
31. (f) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566.
32. (g) Terada, M.; Matsukawa, S.; Mikami, K. J. Chem. Soc., Chem. Commun. 1993, 327.
33. For asymmetric catalysis of (hetero) Diels-Alder reactions: (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
34. (i) Mikami, K.; Terada, M.; Motoyama, Y.; Nakai, T. Tetrahedron: Asymm. 1991, 2, 643.
35. (j) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc., 1994, 116, 2812.
36. For the Mukaiyama aldol reactions of a variety of aldehydes: (k) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039.
37. (l) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077.
38. 3-containing compounds with achiral Lewis acid promoters: Nagai, T.; Kumadaki, I. J. Synth. Org. Chem. Jpn. 1991, 49, 624.
39. Diastereofacial selective aldol reactions with fluorinated carbonyl compounds: (a) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135.
40. (b) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1992, 33, 8147.
41. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
42. We carried out molecular orbital calculations on the protonated aldehydes as a model for 2/ Lewis acid complexes. In the transition states, one of the halogen substituents on the α carbon of aldehydes is most likely to occupy the antiperiplanar region relative to the attacking reagent; Mikami, K.; Shimizu, M. 'Stereoelectronic Rules in Addition Reactions: "Cram's Rule" in Olefinic Systems' in Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Connecticut, U. S. A. Vol. 3, 1993.
43. R molecular modeling workstation) and ab-initio (RHF/6-31G**; Gaussian 90 on HP/Apollo-Series-700) geometry optimizations were carried out without any additional constraints.
44. (a) An ab-initio MO study on α-fluoro propanal in support of the Felkin-Anh model: Wong, S. S.; Paddonrow, M. N. Chem. Commun. 1990, 456.
45. (b) A semi-empirical and ab-initio MO study on fluoroketones: Linderman, R. J.; Jamois, E. A. J. Fluor. Chem. 1991, 53, 79.
46. MNDO and PM3 atomic charges were evaluated from the positive core charges and the numbers of valence electrons. The natural bond orbital (NBO) analysis, instead of conventional Mulliken population analysis, was used for evaluating atomic charges in the ab-initio calculations: Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
47. The reduced carbonyl C-O bond polarity for fluoral might be rationalized by electron withdrawal from oxygen by fluorine substituents. Also see ref. 12b.
48. Only small amounts of allylic alcohols were obtained.
49. (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984, Vol. 3; Chapter 2.
50. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
51. (c) Heathcock, C. H.; Pirrung, M. C.; Sohn, J. E. J. Org. Chem. 1979, 44, 4294.
52. Nagai, T.; Hama, M.; Yoshioka, M.; Yuda, M.; Yoshida, N.; Ando, A.; Koyama, M.; Mikai, T.; Kumadaki, I. Chem. Pharm. Bull. 1989, 37, 177. Also see ref. 7.
53. Mikami, K.; Loh, T.-P.; Nakai, T. Tetrahedron Lett. 1988, 29, 6305.
54. Ab initio MO calculations reveal that bidentate transition structures for the reactions of 2-fluoropropanal or monofluoroacetaldehyde, however, with lithium hydride are stabilized by the electrostatic attraction between Li and F: Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc. Chem. Commun. 1991, 327.
55. Seebach, D.; Zuger, M. F.; Giovannini, F.; Sonneleitner, B.; Fiechter, A. Angew. Chem., Int. Ed. Engl. 1984, 23, 151.
56. Paderes, G. D.; Jorgensen, W. L. J. Org. Chem. 1992, 57, 1904.