Asymmetric catalysis of (Hetero) diels-alder cycloadditions by a modified binaphthol-derived titanium complex

Synlett

Volumn 1995, Issue 9, 1995, Pages 967-968

  Motoyama, Yukihiro ^a   Terada, Masahiro ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

(hetero) Diels Alder reaction; asymmetric catalysis; binaphthol; enantioselectivity; Lewis acid; titanium complex

Indexed keywords

EID: 0003180189     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5138     Document Type: Article

References (27)

1. Morrison, J. D. Asymmetric Synthesis', Acadenic Press: New York, 1984; Vol. 3B.
2. Noyori, R. Asymmetric Catalysis in Organic Synthesis', Wiley: New York, 1994.
3. Noyori, R.; Kitamura, M. in Modern Synthetic Methods 1989; Scheffold, R. ed.; Springer-Verlag: Berlin, 1989; Vol. 5.
4. Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, The Netherlands, 1986.
5. Kagan, H. B. in Comprehensive Organometallic Chemistry; Wilkinson, G. ed.; Pergamon: Oxford, U. K., 1982; Vol. 8.
6. Reviews on asymmetric Diels-Alder reactions
7. Paquette, L. A. in Asymmetric Synthesis; Morrison, J. D. ed.; Academic Press: New York, 1984; Vol. 3B.
8. Oppolzer, W. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. eds.; Pergamon: Oxford, 1991; Vol. 5, p 315.
9. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley: New York, 1990.
10. Taschner, M. J. in Organic Synthesis: Theory and Applications; Hudlicky, T. ed.; JAI Press: London, 1989; Vol. 1.
11. Kagan, H. B. Riant, O. Chem. Rev. 1992, 92, 1007.
12. Mukaiyama, T. Org. React. 1982,28, 203.
13. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977,16, 818.
14. Mukaiyama, T.; Narasaka, K.; Banno, K. J. Am. Chem. Soc., 1974, 96, 7503.
15. Mukaiyama, T.; Banno, K.; Narasaka, K. Chem. Lett. 1973, 1011.
16. Reviews on ene reactions
17. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
18. Snider, B. B. Acc. Chem. Res. 1980,13, 426.
19. Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556.
20. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978,17, 476.
21. Mikami, K.; Motoyama, Y.; Terada, M. Inorg. Chim. Acta 1994, 222, 71.
22. Terada. M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett. 1994,35, 6693.
23. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812.
24. Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991,32, 935.
25. Mikami, K.; Terada, M.; Motoyama, Y.; Nakai, T. Tetrahedron: Asymmetry 1991,2, 643.
26. These observations are in sharp contrast to the remarkable solvent effect observed in the ene reaction (Ref. 5).
27. The cis and trans (85 : 15) mixture of hetero Diels-Alder product with 2c was found not to epimerize after 1 h under the reaction conditions (10 mol% of la at-30 C).