Highly diastereoselective hetero-Diels-Alder reactions of alkenyldihydrooxazoles as an approach to novel pyrimidine derivatives

Chemical Communications

Volumn , Issue 23, 1997, Pages 2311-2312

  Elliott, Mark C ^a   Kruiswijk, Elbertus ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000130283     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a705571d     Document Type: Article

References (16)

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2. Selected review articles: L. F. Tietze and G. Kettschau, Top. Curr. Chem., 1997, 189, 1;
3. D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, 1987.
4. Asymmetric hetero-Diels-Alder reactions of 1-azadienes: R. Beaudegnies and L. Ghosez, Tetrahedron: Asymmetry, 1994, 5, 557;
5. A. Waldner, Tetrahedron Lett., 1989, 30, 3061.
6. Langlois has investigated the use of alkenyloxazolines as dienophiles in asymmetric Diels-Alder cycloadditions: C. Kouklovsky, A. Poulihès and Y. Langlois, J. Am. Chem. Soc., 1990, 112, 6672;
7. Y. Langlois and A. Poulihès, Tetrahedron: Asymmetry, 1991, 2, 1223.
8. W. Seeliger, E. Aufderhaar, W. Diepers, R. Feinauer, R. Nehring, W. Thier and H. Hellmann, Angew. Chem., Int. Ed. Engl. 1966, 5, 875.
9. For a recent report of aza-Diels-Alder reactions of 1-azadienes with isocyanates, see T. Saito, H. Kimura, T. Chonan, T. Soda and T. Karakasa, Chem. Commun., 1997, 1013.
10. For the use of achiral dihydrothiazoles as azadienes, see M. Sakamoto, K. Miyazawa, K. Kuwabara and Y. Tomimatsu, Heterocycles, 1979, 12, 231.
11. B. R. Beno, K. N. Houk and D. A. Singleton, J. Am. Chem. Soc., 1996, 118, 9984;
12. J. W. Storer, L. Raimondi and K. N. Houk, J. Am. Chem. Soc., 1994, 116, 9675.
13. M. A. McCarrick, Y.-D. Wu and K. N. Houk, J. Org. Chem., 1993, 58, 3330;
14. L. F. Tietze, J. Fennen, H. Gießler, G. Schulz and E. Anders, Liebigs Ann. Chem., 1995, 1681.
15. A recent computational study supports this mechanism: W. M. F. Fabian and G. Kollenz, J. Phys. Org. Chem., 1994, 7, 1.
16. J. March, Advanced Organic Chemistry, Wiley Interscience, New York, 4th edn., 1992, p. 978.