The porcine pancreas lipase (PPL) type II catalyzes the aminolysis of benzylidene malonates by regiospecific amidation of substrates and afforded the Z-isomer; no E-isomer or diamide byproducts were observed. PPL also catalyzes Michael addition of acetophenone to various derivatives of chalcones.
Similar content being viewed by others
References
E. N. Kadnikova and A. T. Thakor, Tetrahedron: Asymmetry, 19, 1053 (2008).
L. Veum and U. Hanefeld, Synlett, No. 15, 2382 (2005).
B. Larissegger-Schnell, W. Kroutil, and K. Faber, Synlett, No. 12, 1936 (2005).
Y. Shimada, H. Sato, S. Minowa, and K. Matsumoto, Synlett, No. 3, 367 (2008).
A. P. Nechaev, Yu. A. Sultanovich, N. S. Geiko, S. L. Gramolin, and L. V. Zaitseva, Chem. Nat. Compd., 21, 307 (1985).
E. Busto, V. Gotor-Fernandez, and V. Gotor, Chem. Soc. Rev., 39, 4504 (2010).
E. D. Bergmann, D. Ginsburg, and R. Pappo, The Michael Reaction, in: Organic Reactions, Vol. 10, Eds. C. Adams, A. H. Blatt, V. Boekelheide, A. C. Cope, D. Y. Curtin, F. C. McGrew, and C. Niemann, Wiley, New York, USA, 1959, p. 179.
J. D. Angelo, D. Desmaele, F. Dumas, and A. Guingant, Tetrahedron: Asymmetry, 3, 459 (1992).
B. Alcaide and P. Almendros, Angew Chem. In. Ed., 47, 4632 (2008).
O. Torre, I. Alfonso, and V. Gotor, Chem. Commun., 1724 (2004).
M. Weiâ and H. Groger, Synlett, No. 8, 1251 (2009).
T. Miura, Y. Kawashima, M. Takahashi, Y. Murakami, and N. Imai, Synth. Commun, 37, 3105 (2007).
Acknowledgment
This work was supported by the Research Council of Shahid Beheshti University Tehran, Iran for which the authors are thankful.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2015, pp. 740–742.
Rights and permissions
About this article
Cite this article
Habibi, Z., Yousefi, M., Kheyrabadi, R. et al. Lipase-Catalysed Addition of Pyrrolidine to Chalcone and Benzylidene Malonate Derivatives. Chem Nat Compd 51, 861–864 (2015). https://doi.org/10.1007/s10600-015-1434-1
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-015-1434-1