Diastereoselective Addition of Grignard Reagents to Chiral alfa-Ketoimides Derived from Oppolzer's Sultam

• Autorzy: Raszplewicz K. , Sikorska L. , Kiegiel K. , Bałakier T. , Jurczak J.
• Języki publikacji: EN

Abstrakty

EN

Additions of various Grignard reagents to N-pyruvoyl- (3) and N-phenylglyoxyloyl- (2R)-bornane-10,2-sultam (4) under thermal and Lewis-acid catalytic conditions are studied. High diastereoselectivity was observed in these reactions, and in the case of vinylmagnesium bromide additions to -ketoimide 4 a change of direction of asymmetric induction was found.

Słowa kluczowe

EN

Grignard reaction; asymmetric synthesis; diastereoselectivity; chiral auxiliary

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 12
• Strony: 1901--1907
• Opis fizyczny: Bibliogr. 12 poz.

Twórcy

autor

Raszplewicz K.

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

autor

Sikorska L.

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

autor

Kiegiel K.

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

autor

Bałakier T.

• 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.(a)Bauer T., Chapuis C., Kozak J. and Jurczak J., Helv. Chim. Acta, 72, 482 (1989); (b) Bauer T., Jeżewski A., Chapuis C. and Jurczak J., Tetrahedron : Asymmetry, 7, 1385 (1996).
• 2.(a) Bauer T., Kozak J., Chapuis C. and Jurczak J., J. Chem. Soc., Chem. Commun., 1178 (1990); (b)Freund R., Allagiannis C., Schoenholzer P. and Bemauer K., Helv. Chim. Acta, 77, 615 (1994);(c)Bauer T., Tetrahedron: Asymmetry, 7, 981 (1996); (d) Bauer T., Chapuis C., Jeżewski A., Kozak J. and Jurczak J., Tetrahedron: Asymmetry, 7, 1391 (1996); (e) Bauer T., Jeżewski A., Kozak J. and Ju¬czak J., Tetrahedron: Asymmetry, 7,1405 (1996); (0 Jurczak J. and Jeżewski A., Tetrahedron. Asymmetry, 7, 1413 (1996); (g) Czarnocki Z., Mieczkowski J.B., Kiegiel J. and Araźny Z., Tetrahedron : Asymmetry, 6, 2899 (1995); (h) Bauer T., Tetrahedron, 53, 4763 (1997); (i) Jeżewski A., Chajewska K., Wielogórski Z. and Jurczak J., Tetrahedron : Asymmetry, 8, 1741 (1997); (j) Bauer T., Szymański S., Jeżewski A., Gluziński R and Jurczak J., Tetrahedron: Asymmetry, 8, 2619 (1997).
• 3.Oppolzer W., Chapuis C. and Bernardinelli B., Helv. Chim. Acta, 67, 1397 (1984).
• 4.Bauer T., Chapuis C., Kiegiel J., Krajewski J. W., Piechota K., Urbańczyk-Lipkowska Z. and Jurczak J., Helv. Chim. Acta, 79, 1059 (1996).
• 5.(a) Ward R.S., Pelter A., Goubet D. and Pritchard M.C., Tetrahedron: Asymmetry, 6,93 (1995); (b) Ward R.S., Pelter A., Goubet D. and Pritchard M.C., Tetrahedron: Asymmetry, 6, 596 (1995).
• 6.Raszplewicz K., Sikorska L., Kiegiel K. and Jurczak J., Polish J. Chem., 76, 1595 (2002).
• 7.Kiegiel K., Prokopowicz P. and Jurczak J., Synth. Commun., 29, 3999 (1999).
• 8.Ferraboschi P., Casati S., Grisenti S. and Santaniello E., Tetrahedron: Asymmetry, 5, 1921 (1994).
• 9.Davis F.A., Reddy G.V., Kumar A. and Haque M.S., J. Org. Chem., 60, 6148 (1995).
• 10.Kiegiel K. and Jurczak J., Tetrahedron Lett., 40, 1009 (1999).
• 11.Wipf P. and Xu W., Tetrahedron Lett., 35, 5197 (1994).
• 12.Agami C., Couty F. and Leguesne Ch., Tetrahedron, 51,4043 (1995).