Rational design of a new chiral Lewis acid catalyst for enantioselective Diels-Alder reaction: Optically active 2-dichloroboryl-1,1′-binaphthyl

Synlett

Volumn , Issue 10, 1998, Pages 1053-1056

  Ishihara, Kazuaki ^a   Inanaga, Kazato ^a   Kondo, Shoichi ^a   Funahashi, Miyuki ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000503136     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1860     Document Type: Article

References (28)

1. For a recent review, see: Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: London, 1995; Vol. 1 p. 29.
2. For recent articles on enantioselective Lewis acid-catalyzed Diels-Alder reactions of dienes and α,β-unsaturated aldehydes, see: (a) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
3. (b) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502.
4. (c) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H.; Ohashi, S.; Inagaki, S. J. Org. Chem. 1997, 62, 3026.
5. (c) Corey, E. J.; Lee, T. W. Tetrahedron Lett. 1997, 38, 5755.
6. For previous articles on enantioselective Lewis acid-catalyzed Diels-Alder reactions of dienes and α,β-unsaturated esters, see: (a) Hashimoto, S.-H.; Komeshima, N.; Koga, K. J. Chem. Soc. Chem. Commun. 1979, 437.
7. (b) Rebiere, F.; Riant, O.; Kagan, H. B. Tetrahedron: Asymmetry 1990,1, 199.
8. (c) Bir, G.; Kaufmann, D. J. Organomet. Chem. 1990, 390, 1.
9. (d) Hawkins, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794;
10. Hawkins, J. M.; Loren, S.; Nambu, M. J. Am. Chem. Soc. 1994, 116, 1657.
11. (e) Devine, P. N.; Taeboem, O. J. Org. Chem. 1992, 57, 396.
12. (f) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501.
13. Very recently, Wulff and co-workers reported the highly enantioselective Diels-Alder reaction of cyclopentadiene and methyl acrylate catalyzed by a VAPOL-aluminum catalyst in the presence of an additional ligand. Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 779, 10551.
14. Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: New York, 1988.
15. Recently, the synthesis of racemic 5a has been announced, see: (a) Schilling, B.; Kaiser, V.; Kaufmann, D. E. Chem. Ber. 1997, 130, 923.
16. (b) Schilling, B.; Kaufmann, D. E. Eur. J. Org. Chem. 1998, 701.
17. Sasaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300.
18. 2O) δ 125.8, 125.9, 126.2, 126.3, 126.80, 126.84, 127.5, 127.7, 127.8, 129.0, 129.4, 131.5, 131.9, 132.1, 134.1, 135.1, 138.1, 139.5, 139.6, 140.65, 140.73, 144.2.
19. For the dehydroxylation of phenols by cleavage of their diethyl phosphate esters, see: Rossi, R. A.; Bunnett, J. F. J. Org. Chem. 1973, 38, 2314.
20. (a) Katz, H. E. J. Org. Chem. 1985, 50, 2575.
21. (b) Cole, T. E.; Quintanilla, R.; Smith, B. M.; Hurst, D. Tetrahedron Lett. 1992, 33, 2761.
22. Method A: A dry, 25-mL round flask fitted with a stirring bar and a reflux condenser was charged with chiral boronic acid 5a (14.9 mg, 0.05 mmol) and dry methanol (1 mL). An argon atmosphere was secured, and the solution was brought to reflux. After being refluxed for 2 h, the methanol and water generated were removed under vacuum at room temperature. After the above treatment of 5a with methanol was repeated three times, the resulting solid was dissolved in dichloromethane (150 μL) and boron trichloride solution in hexane (1 M, 150 μL, 0.15 mmol) at 0°C. After being stirred at 0°C for 12 h, the volatile boron compounds and solvents were removed under vacuum at room temperature. The treatment with boron trichloride was repeated twice. The residual oil obtained as 7a was immediately used as a catalyst for the Diels-Alder reaction without isolation.
23. 6) δ 57.4.
24. S-trans enone conformation with the metal located anti to the alkoxy group has been observed for complexes of α,β-unsaturated esters with Lewis acids: (a) Lewis, F. D.; Oxman, J. D.; Gibson, L. L.; Hampsch, H. L.; Quillen, S. L. J. Am. Chem. Soc. 1986, 108, 3005.
25. (b) Lewis, F. D.; Quillen, S. L.; Hale, P. D.; Oxman, J. D. J. Am. Chem. Soc. 1988, 110, 1261.
26. (c) see reference 3b.
27. For preparation of 2,2-dimethyl-5-methylene-1,3-dioxolan-4-one, see: (a) Bailey, W. J.; Feng, P. Polym. Prepr. 1987, 28, 154.
28. (b) Mattay, J.; Kneer, G.; Mertes, J. Synlett 1990, 145.