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

Szymański, S.; Marzec, M.; Jurczak, J.

Artykuł - szczegóły

Tytuł artykułu

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

Autorzy

Szymański S. , Marzec M. , Jurczak J.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

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

[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).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ1-0020-0094