Synthesis and Structure of N,N'-Diaryl Derivatives of trans-1,2-Diaminocyclohexane

• Autorzy: Kwit M. , Kubicki M. , Borowiak T. , Gawroński J.
• Języki publikacji: EN

Abstrakty

EN

Synthesis of N,N_-diaryl derivatives of trans-1,2-diaminocyclohexane (DACH) by palladium- catalyzed aromatic nucleophilic substitution reactions is described. The conformation of the N-acetylated N,N_-diaryl derivatives of DACH has been studied by the computational, circular dichroism and X-ray diffraction methods. Reversal of the relative orientation of the N-aryl residues due to N-acetylation has been established.

Słowa kluczowe

EN

trans-1,2-diaminocyclohexane; palladium; N-arylation; conformation

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2003
• Tom: Vol. 77 / nr 11
• Strony: 1669--1682
• Opis fizyczny: Biubliogr. 20 poz., rys.

Twórcy

autor

Kwit M.

• Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland

autor

Kubicki M.

• Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland

autor

Borowiak T.

• Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland

autor

Gawroński J.

• Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland

Bibliografia

• 1. a) Jacobsen E.N. and Wu M.H., in Comprehensive Asymmetric Catalysis, Jacobsen E.N., Pfaltz A., and Yamamoto H. (eds) Springer-Verlag, Berlin 2000; b) Jacobsen E.N., in Comprehensive Organometallic Chemistry II, Wilkinson G., Stone F.G.A., Abel E.W., and Hegedus L.S. (eds), Pergamon Press, NY 1995;c)KatsukiT.,J. Mol. Cat. A. Chemical, 113,87(1996); d) Katsuki T., Adv. Synth. Catal, 344,131 (2002) ; e) Jacobsen E.N., Acc. Chem. Res., 33, 421 (2000).
• 2. Trost B.M. and Lee C., in Catalytic Asymmetric Synthesis, Ojima I. (ed), Willey-VCH, NY 2000.
• 3. a) Gawroński J., Kolbon H., Kwit M. and Katrusiak A., J. Org. Chem., 65, 5768 (2000); b) Kwit M. and Gawroński J., Tetrahedron: Asymmetry, 14, 1303 (2003).
• 4. a) Gawroński J., Kaźmierczak F., Gawrońska K., Rychlewska U., Norden B. and Holmen A., J. Am Chem. Soc., 120, 12083 (1998); b) Gawroński J., Brzostowska M., Kacprzak K., Kolbon H. and Skowronek P., Chirality, 12, 263 (2000).
• 5. Frost C.G. and Mendonca P., Tetrahedron: Asymmetry, 10, 1831 (1999).
• 6. Gangopadhyay P. and Radhakrishan T.P., Angew. Chem. Int. Ed., 40, 2451 (2001).
• 7. Guram A.S., Rennels R.A. and Buchwald S.L., Angew. Chem. Int. Ed., 34, 1348 (1995).
• 8. Hartwig J.F., Richards S., Baraflano D. and Paul F., J. Am. Chem. Soc., 118, 3626 (1996).
• 9. a) Wolfe J.P., Wagaw S., Marcoux J-F. and Buchwald S.L., Acc. Chem. Res., 31, 805 (1998); b) Yang
• B. H. and Buchwald S.L., J. Organomet. Chem., 576, 125 (1999); c) Frost C.G. and Mendonęa P.J., J. Chem. Soc., Perkin Trans. 1,2615 (1998).
• 10. Rivas F.M., Riaz U. and Diver S.T., Tetrahedron: Asymmetry, 11, 1703 (2000).
• 11. Beletskaya I.P., Bessmertnykh A.G. and Guilard R., Tetrahedron Lett., 40, 6393 (1999).
• 12. Kwit M. and Gawroński J., Tetrahedron, accepted for publication.
• 13. a) Gawroński J., Kolbon H. and Kwit M., Enantiomer, 7,85 (2002); b) Borowiak T., unpublished results.
• 14. Khan A.Z.-Q., Ivanova G.I., Spassov S.L. and Sandström J., Acta Chem. Scand., 50, 938 (1996).
• 15. Gaussian 98, Revision A.10, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A.. Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Jr., Stratmann R.E., Burant J.C., Dapprich S.. Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Salvador P., Dannenberg J.J., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I. , Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A.. Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head- Gordon M., Replogle E.S. and Pople J.A., Gaussian, Inc., Pittsburgh PA, 2001.
• 16. Oxford Diffraction Poland Sp. CrysAlis CCD program system ver. 1. 169. Wroclaw, Poland (2002).
• 17. Oxford Diffraction Poland Sp. CrysAlis Red: CCD data reduction program system ver. 1.169. Wroclaw. Poland (2002).
• 18. Blessing R.H.,7. AppI.Crystallogr., 22, 396 (1989).
• 19. Sheldrick G.M., SHELXS-97, Program for Solution of the Crystal Structures, University of Göttingen, Germany (1997).
• 20. Sheldrick G.M., SHELXL-97, Program for Refinement of the Crystal Structures, University of Göttingen, Germany (1997).