Diastereoselective [4+2} Cycloaddition of Cyclopentadiene to N-Tosyliminoacetyl Derivatives of Chiral Secondary Alcohols

• Autorzy: Szymański S. , Marzec M. , Jurczak J.
• Języki publikacji: EN

Abstrakty

EN

Syntheses of five N-tosylimines of chiral glyoxylates are described. The N-tosylimines obtained were used as dienophiles in the Lewis acid-catalyzed asymmetric hetero- -Diels-Alder reaction with cyclopentadiene to afford cycloadducts with moderate diastereoisomeric excess.

Słowa kluczowe

EN

[4+2] cycloaddition; N-tosylimines; cyclopentadiene; Lewis acids; diastereoselectivity

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 6
• Strony: 831--837
• Opis fizyczny: Bibliogr. 23 poz., rys.

Twórcy

autor

Szymański S.

• Department of Chemistry, Warsaw University, 02-093 Warsaw, Poland

autor

Marzec M.

• Department of Chemistry, Warsaw University, 02-093 Warsaw, Poland

autor

Jurczak J.

• Department of Chemistry, Warsaw University, 02-093 Warsaw, Poland
• Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland

Bibliografia

• 1. Weinreb S.N. and Steib R.R., Tetrahedron, 28, 791 (1982).
• 2. Ward S.E., Holmes A.B. and McCague R., Chem. Commun., 2085 (1997).
• 3. Zhong W., Xie W., Fang J. and Wong P.G., Tetrahedron Lett., 40, 7929 (1999).
• 4. Perrin V., Riverson V., Traversa C., Balma C. and Gore J., J. Chem. Res. (S), 60 (2000).
• 5. For a recent review on chiral aza-Diels-Alder reactions, see: Jargensen K.A., Angew. Chem. Int. Ed., 39, 3558 (2000).
• 6. Danheiser R.L., J. Org. Chem., 63, 7840 (1998).
• 7. Ager D., Cooper N., Cox G.G., Garro-Helion F. and Harwood L.M., Tetrahedron: Asymmetry, 7, 2563 (1996) .
• 8. Yao S., Saaby S., Hazel R.G. and J0rgensen K.A., Chem. Eur. J., 6, 2435 (2000).
• 9. Morgan P.E., McCargue R. and Whiting A., J. Chem. Soc., Perkin Trans. 7,515 (2000).
• 10. Waldmann H. and Braun M., Liebigs Ann. Chem., 1045 (1991).
• 11. Stella L., Abraham H., Feneau-Dupont J., Tinant B. and Leclercq J.P., Tetrahedron Lett., 31, 2063 (1990).
• 12. Bailey P.D., Wilson R.D. and Brown G.R., J. Chem. Soc., Perkin Trans 1, 1337 (1991).
• 13. Blanco J.M., Caamano O., Fernandez F., Garcia-Mera X., Lopez C., Rodriguez G., Rodriguez-Borges J.E. and Rodriguez-Hergueta A., Tetrahedron Lett., 39, 5663 (1998).
• 14. Bauer T., Szymański S., Jeżewski A., Gluziński P. and Jurczak J., Tetrahedron: Asymmetry, 8, 2619 (1997) .
• 15. Szymański S., Chapuis C. and Jurczak J., Tetrahedron: Asymmetry, 12, 1939 (2001).
• 16. Jurczak J. and Zamojski A., Roczn. Chem., 44, 2257 (1970).
• 17. Freund R., Martinovic S. and Bemauer K., Helv. Chim. Acta, 75, 282 (1992).
• 18. Gao Y., Lane-Bell P. and Vederas J.C., J. Org. Chem., 63, 2133 (1998).
• 19. Shida N., Kabuto C., Niva T., Ebata T. and Yamamoto Y., J. Org. Chem., 59, 4068 (1994).
• 20. Czapla A., Chajewski A., Kiegiel K., Bauer T., Wielogórski Z., Urbańczyk-LipkowskaZ. and Jurczak J., Tetrahedron: Asymmetry, 10, 2101 (1999).
• 21. Breslow R. and Rideout D., J. Am. Chem. Soc., 102, 7816 (1980).
• 22. Oppolzer W., Chapuis C., Mao Dao G., Reichlin D. and Godel T., Tetrahedron Lett., 23, 4781 (1982).
• 23. Still W.C., Kahn M. and Mitra A., J. Org. Chem., 47, 13 (1982).